Cesium carbonate → 3-(4-{2-[4-chloro(methyl)anilino]ethoxy}-3-methoxyphenyl)-6-(4-chlorophenyl)thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1181344Notes

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=CC(S(O[CH2:37][CH2:38][N:39]([CH3:47])[C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.C(O)C>CN(C=O)C>[Cl:46][C:43]1[CH:44]=[CH:45][C:40]([N:39]([CH3:47])[CH2:38][CH2:37][O:24][C:21]2[CH:22]=[CH:23][C:18]([N:13]3[C:14](=[O:17])[C:15]4[S:16][C:8]([C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=5)=[CH:9][C:10]=4[N:11]=[CH:12]3)=[CH:19][C:20]=2[O:25][CH3:26])=[CH:41][CH:42]=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 can be found in the section detailing the preparation of Example K1) in DMF was added 2-[4-chloro(methyl)anilino]ethyl p-toluenesulfonate (170 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 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 (136 mg, 98%). 1H NMR (DMSO-D6) δ 3.00 (3H, s), 3.77 (5H, m), 4.21 (2H, m), 6.81 (2H, d, J=9.0 Hz), 7.02-7.20 (5H, m), 7.58 (2H, d, J=8.6 Hz), 7.95 (3H, m), 8.39 (1H, s). Calcd. for C28H23Cl2N3O3S×3HCl: C, 50.81; H, 3.96; N; 6.35. Found: C, 50.91; H, 3.95; N, 6.23.

Workup

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

Sources & evidence

ORD record: ord-d165f3513dcd473c97d7398d04b57f56
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285557B2

Reaction notes

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