Formamidine acetate → 4-(Dimethoxymethyl)pyrimidine

HRID 332008Notes

Reaction equation

HRID 332008 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]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 5709580((1E)-4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamine

Product 1

HCID 124402404-(Dimethoxymethyl)pyrimidineYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic extracts were then dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification
  7. distillationby distillation

Sources & evidence

ORD record
ord-a16d362e903c4f1cbb1e798c1f56208a
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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