Dimethylformamide → 3-[4-(3-Dimethylamino-pyrrolidin-1-yl)-phenyl]-6-propoxymethyl-3H-thieno[3,2-d]pyrimidin-4-one

HRID 72240Notes

Reaction equation

[CH3:1][N:2]([CH3:26])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C:19](=[O:20])[C:18]4[S:21][C:22]([CH2:24][OH:25])=[CH:23][C:17]=4[N:16]=[CH:15]3)=[CH:10][CH:9]=2)[CH2:4]1.[H-].[Na+].CN(C=O)C.Br[CH2:35][CH2:36][CH3:37]>C(OCC)(=O)C.O>[CH3:1][N:2]([CH3:26])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[C:19](=[O:20])[C:18]4[S:21][C:22]([CH2:24][O:25][CH2:35][CH2:36][CH3:37])=[CH:23][C:17]=4[N:16]=[CH:15]3)=[CH:12][CH:13]=2)[CH2:4]1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 3-[4-(3-Dimethylamino-pyrrolidin-1-yl)-phenyl]-6-hydroxymethyl-3H-thieno[3,2-d]pyrimidin-4-one (50.0 mg), sodium hydride (5.24 mg) and DMF (1 mL) was stirred at 0° C. for 15 min. Then 1-bromopropane (22.0 mg) was added, the solution was warmed to room temperature and stirred for 2 h. Water and ethyl acetate were added and the aqueous phase was extracted with ethyl acetate several times. The combined organic phase was dried over sodium sulfate and the solvent removed in vacuo. The crude product was purified by preparative HPLC. The product with the molecular weight of 412.55 (C22H28N4O2S) was obtained in this way; MS (ESI): 413 (M+H+).

Workup

temperaturethe solution was warmed to room temperature
stirringstirred for 2 h
extractionthe aqueous phase was extracted with ethyl acetate several times
dry with materialThe combined organic phase was dried over sodium sulfate
customthe solvent removed in vacuo
customThe crude product was purified by preparative HPLC
customThe product with the molecular weight of 412.55 (C22H28N4O2S) was obtained in this way

Sources & evidence

ORD record: ord-58d9b858519f4d48a7ab935cfbb0e9f1
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828991B2

Reaction notes

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