Guanidine Hydrochloride → 4-(1,1-Dimethoxyethyl)pyrimidin-2-amine

HRID 1845858Notes

Reaction equation

HRID 1845858 reaction equation
CN(C)[CH:3]=[CH:4][C:5](=O)[C:6]([O:10][CH3:11])([O:8][CH3:9])[CH3:7].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:21][C:22]([NH2:24])=[NH:23]>C(O)C>[CH3:9][O:8][C:6]([C:5]1[CH:4]=[CH:3][N:21]=[C:22]([NH2:24])[N:23]=1)([O:10][CH3:11])[CH3:7]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 5668111-Penten-3-one, 1-(dimethylamino)-4,4-dimethoxy-

Product 1

HCID 135822684-(1,1-Dimethoxyethyl)pyrimidin-2-amineYield 62.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(dimethylamino)-4,4-dimethoxypent-1-en-3-one (1a) (34.29 g) was dissolved in ethanol (750 mL). Potassium carbonate (65.3 g) and guanidine hydrochloride (20.77 g) were added and the resulting suspension heated to reflux overnight. The reaction mixture was concentrated in vacuo, the residue was stirred with water overnight, filtered and dried in a vacuum oven at 40° C. overnight to afford the title compound (21.01 g) as a white solid. The filtrate was extracted with dichloromethane (3×700 mL) and the combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford a further crop (10.6 g) of the title compound.

Workup

  1. temperaturethe resulting suspension heated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. filtrationfiltered
  5. customdried in a vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-f41f0e4475744640919d6cedb81c4085
Source dataset
uspto-grants-2015_02
Patent number
US08952001B2

Reaction notes

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