Formamidine acetate → 4-(Dimethoxymethyl)pyrimidine

HRID 1896650Notes

Reaction equation

HRID 1896650 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)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of (3E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (C10) (147 g, 0.85 mol) and formamidine acetate (131 g, 1.26 mol) was heated at 110-120° C. for 4 hours. After cooling to room temperature, the reaction was poured into water (250 mL) and extracted with chloroform (5×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Distillation of the residue under vacuum afforded the product as an oil. Yield: 84 g, 0.54 mol, 64%. Boiling point: 45-50° C./0.2 torr. NMR data was obtained using the product of a reaction run under similar conditions. 1H NMR (400 MHz, CDCl3) δ 3.30 (s, 6H), 5.21 (s, 1H), 7.46 (dd, J=5.1, 1.4 Hz, 1H), 8.68 (d, J=5.1 Hz, 1H), 9.12 (d, J=1.4 Hz, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with chloroform (5×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. distillationDistillation of the residue under vacuum

Sources & evidence

ORD record
ord-5278bc2bbb2249beb3ace9f146651611
Source dataset
uspto-grants-2013_08
Patent number
US08518944B2

Reaction notes

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