Formamidine acetate → 4-(Dimethoxymethyl)pyrimidine
Reaction equation
[CH3:1][N:2](C)/[CH:3]=[CH:4]/[C:5](=O)[CH:6]([O:9][CH3:10])[O:7][CH3:8].C(O)(=O)C.C(N)=[NH:18]>O>[CH3:8][O:7][CH:6]([O:9][CH3:10])[C:5]1[CH:4]=[CH:3][N:2]=[CH:1][N:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A mixture of (E)-4-dimethylamino-1,1-dimethoxy-but-3-en-2-one (49.6 g, 286 mmol) and formamidine acetate (44.7 g, 429 mmol) was heated at 120° C. for 4 h. After cooling to room temperature the mixture was poured into water and extracted with dichloromethane. The combined organic extracts were then dried over sodium sulfate, filtered and evaporated. Purification by distillation afforded the title product (31 g, 70%) as a colourless liquid. Bp 59-60° C. at 1.3 mbar. MS: m/e=155.0 [M+H]+.
Workup
- temperatureAfter cooling to room temperature the mixture
- extractionextracted with dichloromethane
- dry with materialThe combined organic extracts were then dried over sodium sulfate
- filtrationfiltered
- customevaporated
- customPurification
- distillationby distillation
Sources & evidence
- ORD record
- ord-e921c82f583a41f086b3ee3d56a2046d
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877783B2
Reaction notes
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