1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → 1-(5-Bromothien-2-ylmethyl)-5-chloropyrimidin-2-one

HRID 434655Notes

Reaction equation

C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[NH:22][CH:23]=1.[Br:25][C:26]1[S:30][C:29]([CH2:31]O)=[CH:28][CH:27]=1>CN(C)C=O>[Br:25][C:26]1[S:30][C:29]([CH2:31][N:20]2[CH:19]=[C:18]([Cl:17])[CH:23]=[N:22][C:21]2=[O:24])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 40 °C

Procedure

N,N-Dimethylformamide dineopentyl acetal (2.25 ml) was added to a stirred suspension of 5-chloropyrimidin-2-one (653 mg) and 5-bromo-2-hydroxymethylthiophene (1.351 g) in dry N,N-dimethylformamide (12.5 ml) under nitrogen and then the mixture was heated at 40° C. After 2 h the temperature was increased to 80° C. After 4 h the reaction mixture was evaporated to dryness and the residue triturated with diethyl ether. The solid was collected and crystallised from acetone to give off white crystals of the title pyrimidinone (691 mg), m.p. 217°-220° C., λmax (EtOH) 243.5 nm (ε 13,810), 336 nm (ε 1,190).

Workup

temperatureAfter 2 h the temperature was increased to 80° C
customAfter 4 h the reaction mixture was evaporated to dryness
customthe residue triturated with diethyl ether
customThe solid was collected
customcrystallised from acetone

Sources & evidence

ORD record: ord-8983776e7a9a42ca87ea3ed0d4d526b3
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04399140

Reaction notes

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