Cesium carbonate → HCID 58980847, compound

HRID 1181345Notes

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][C@@H:38]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH3:39])(=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][CH2:39][C@@H:38]([NH:40][C:41](=[O:42])[O:43][C:44]([CH3:45])([CH3:47])[CH3:46])[CH3:37])=[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]pyrimidin4(3H)-one (0.29 g, 0.75 mmol, the preparation of which can be found in the section detailing the preparation of Example K1) in DMF was added (2S)-2-[(tert-butoxycarbonyl)amino]propyl toluenesulfonate (0.5 g, 1.50 mmol) and cesium carbonate (0.72 g, 2.25 mmol) and the mixture was stirred with heating at 75° C. for 12 h. The reaction was allowed to cool and 25 mL of a solution of 20% water/ethanol was added. The resulting precipitate was filtered and dried in a vacuum oven to give the product (200 mg, 49%). 1H NMR (DMSO-D6) δ 1.15 (3H, d, J=6.1 Hz), 1.40 (9H, s), 3.79 (6H, m), 7.22-7.20 (3H, m), 7.59 (2H, d, J=8.4 Hz), 7.95-7.99 (3H, m) 8.40 (1H, s). LCMS m/z=542 (m+H+).

Workup

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

Sources & evidence

ORD record: ord-7ddc107fd79c47da9f31f6ab5f3dd7d5
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285557B2

Reaction notes

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