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

HRID 1181342Notes

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.Cl[CH2:28][CH2:29][N:30]([CH2:38][CH3:39])[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=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][CH2:28][CH2:29][N:30]([CH2:38][CH3:39])[C:31]5[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=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 can be found in the section detailing the preparation of Example K1) in DMF was added N-(2-chloroethyl)-N-ethyl-3-methylaniline (99 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 (58 mg, 42%). 1H NMR (DMSO-D6) δ 1.13 (3H, t, J=7.0 Hz), 2.24 (3H, s), 3.45 (2H, q, J=7.0 Hz), 3.70 (2H, d, J=5.8 Hz), 3.79 (3H, s), 4.16 (2H, d, J=5.8 Hz), 6.43 (1H, t, J=7.3 Hz), 6.57 (2H, m), 7.02-7.20 (4H, m), 7.60 (2H, d, J=8.6 Hz), 7.96 (3H, m), 8.39 (1H, s). LCMS m/z=546 (m+H+).

Workup

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

Sources & evidence

ORD record: ord-8f69085881ec4567858f2a4976412344
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285557B2

Reaction notes

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