2-(4-Bromophenoxy)-3-isopropyl-5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one

In the title compound, C19H19BrN2O2S, the central thienopyrimidine ring system is essentially planar, with a maximum displacement of 0.068 (3) Å. The attached cyclohexene ring adopts a half-chair conformation. The molecular conformation and crystal packing are stabilized by three intramolecular C—H⋯O hydrogen bonds and two C—H⋯π interactions.

In the title compound, C 19 H 19 BrN 2 O 2 S, the central thienopyrimidine ring system is essentially planar, with a maximum displacement of 0.068 (3) Å . The attached cyclohexene ring adopts a half-chair conformation. The molecular conformation and crystal packing are stabilized by three intramolecular C-HÁ Á ÁO hydrogen bonds and two C-HÁ Á Á interactions.

Related literature
For background to the use of pyrimidine derivatives as drugs, see: Ding et al. (2004). For a description of the Cambridge Structural Database, see: Allen (2002). For a related structure, see: Zeng et al. (2006). Symmetry code: (i) x; y À 1; z. Cg1 and Cg2 are the centroids of the thiophene (S1/C5-C8) and pyrimidine (N1/N2/C7-C10) rings, respectively.  The cyclohexene ring adopts a half-chair conformation. The crystal packing is stabilized by three intramolecular C-H···O hydrogen bonds and two C-H···π interactions (Table 1). There exist no intermolecular hydrogen bonding interactions and no π-π stackings.

S2. Experimental
To a solution of iminophosphorane (1.45 g, 3 mmol) in anhydrous dichloromethane (15 ml) was added iso-propyl isocyanate (3 mmol) under dry nitrogen at room temperature. After the reaction mixture was left unstirred for 48 h at room temperature, the solvent was removed off under reduced pressure and ether/petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solvent was removed, and the residue was dissolved in CH 3 CN (15 ml). After adding 4-Br-PhOH (3.1 mmol) and excess K 2 CO 3 to the solution of carbodiimide, The mixture was stirred for 24 h at room temperature, the solution was condensed and the residue was recrystallized by EtOH to give the title compound, (I), in yield of 80% (m.p. 478 K). Elemental analysis calculated for C 19 H 19 BrN 2 O 2 S: C 54.42, H 4.57, N 6.68.
Found: C 54.56, H 4.42, N 6.53. Crystals suitable for single crystal X-ray diffraction were obtained by vapor diffusion of hexane and dichloromethane (1:3 v/v) at room temperature.

S3. Refinement
H atoms were placed at calculated positions and treated as riding atoms, with C-H = 0.93-0.98 Å, and U iso (H) = 1.2U eq (C) for CH or 1.5U eq (C) for CH 3 .  View of the molecule of (I) showing the atom-labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H-atoms are represented by circles of arbitrary size.  (8) Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.