Cesium carbonate → 6-(4-chlorophenyl)-3-{3-methoxy-4-[2-(methylanilino)ethoxy]phenyl}thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1181341Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:25][CH3:26])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C1(C)C(S(O[CH2:37][CH2:38][N:39]([CH3:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)(=O)=O)=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.C(O)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:37][CH2:38][N:39]([CH3:46])[C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)=[C:20]([O:25][CH3:26])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 6-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one (96 mg, 0.25 mmol, the preparation of which may be found in Example K1) in DMF was added 2-(methylanilino)ethyl toluenesulfonate (153 mg, 0.50 mmol) and cesium carbonate (0.24 g, 0.75 mmol) and the mixture was stirred with heating at 75° C. for 12 h. The reaction was allowed to cool and a 10 mL solution of 20% water/ethanol was added. The resulting precipitate was filtered and dried in a vacuum oven to give the title compound (104 mg, 80%). 1H NMR (DMSO-D6) δ 3.01 (3H, s), 3.78 (5H, m), 4.18 (2H, t, J=3.7 Hz), 6.63 (1H, t, J=7.3 Hz), 6.78 (2H, d, J=7.2 Hz), 7.02-7.20 (5H, m), 7.60 (2H, d, J=8.6 Hz), 7.96 (3H, m), 8.39 (1H, s). LCMS m/z=518 (m+H+). Calcd. for C28H24ClN3O3S×1H2O: C, 62.74; H, 4.89; N, 7.84. Found: C, 62.76; H, 4.65; N, 7.82.

Workup

temperatureto cool
filtrationThe resulting precipitate was filtered
customdried in a vacuum oven

Sources & evidence

ORD record: ord-37015ba153194d1c8a3b907ddabbdd1e
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285557B2

Reaction notes

Loading…