Water → 3-[4-((R)-3-Dimethylaminopyrrolidin-1-yl)phenyl]-6-piperidin-1-yl-3H-thieno[3,2-d]pyrimidin-4-one

HRID 72212Notes

Reaction equation

Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:22][CH2:21][C@@H:20]([N:23]([CH3:25])[CH3:24])[CH2:19]4)=[CH:14][CH:13]=3)[CH:6]=[N:5][C:4]=2[CH:3]=1.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.O>C(OCC)(=O)C>[CH3:24][N:23]([CH3:25])[C@@H:20]1[CH2:21][CH2:22][N:18]([C:15]2[CH:16]=[CH:17][C:12]([N:7]3[C:8](=[O:11])[C:9]4[S:10][C:2]([N:26]5[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)=[CH:3][C:4]=4[N:5]=[CH:6]3)=[CH:13][CH:14]=2)[CH2:19]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-bromo-3-[4-((R)-3-dimethylaminopyrrolidin-1-yl)phenyl]-3H-thieno[3,2-d]pyrimidin-4-one (40 mg) and piperidine (492 mg) was heated at 100° C. for 2 days. Water and ethyl acetate were then added, and the organic phase was washed twice with water. The ethyl acetate phase was dried over sodium sulfate and the solvent was removed in vacuo. The residue was purified by preparative HPLC. The product with the molecular weight of 423.58 (C23H29N50S) was obtained in this way; MS (ESI): 424 (M+H+).

Workup

washthe organic phase was washed twice with water
dry with materialThe ethyl acetate phase was dried over sodium sulfate
customthe solvent was removed in vacuo
customThe residue was purified by preparative HPLC
customThe product with the molecular weight of 423.58 (C23H29N50S) was obtained in this way

Sources & evidence

ORD record: ord-81eb96523a414840b71293a65f0edb3a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828991B2

Reaction notes

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