Triethylamine → 4-Amino-2-(3-methoxy-1-methylpropylamino)-5,6-dichloropyrimidine

HRID 1248889Notes

Reaction equation

HRID 1248889 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH:5]([NH2:7])[CH3:6].C(N(CC)CC)C.[NH2:15][C:16]1[C:21]([Cl:22])=[C:20]([Cl:23])[N:19]=[C:18](Cl)[N:17]=1>C1(C)C=CC=CC=1>[NH2:15][C:16]1[C:21]([Cl:22])=[C:20]([Cl:23])[N:19]=[C:18]([NH:7][CH:5]([CH3:6])[CH2:4][CH2:3][O:2][CH3:1])[N:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 158501962,5,6-Trichloropyrimidin-4-amineHCID 178564404-Methoxybutan-2-amine

Product 1

HCID 136496944-Amino-2-(3-methoxy-1-methylpropylamino)-5,6-dichloropyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.4 g (0.033 mole) of 3-methoxy-1-methylpropylamine and 3.3 g (0.033 mole) of triethylamine are successively added dropwise to a solution of 6.5 g (0.033 mole) of 4-amino-2,5,6-trichloropyrimidine in 200 ml of toluene and the mixture is heated to the boil for five hours. When it has cooled, the reaction mixture is washed with water and the organic phase is dried over sodium sulphate and concentrated. The crude product thus obtained is purified by chromatography over silica gel (length of column: 80 cm, diameter: 5 cm), using ethyl acetate and petroleum ether (1:1). In addition to 4-amino-6-(3-methoxy-1-methylpropylamino)-2,5-dichloropyrimidine (1st fraction, melting point 62° C.), 1.5 g (17.2% of theory) (2nd fraction, melting point 96° C.) of the desired pyrimidine are obtained.

Workup

  1. temperaturethe mixture is heated to the boil for five hours
  2. temperatureWhen it has cooled
  3. washthe reaction mixture is washed with water
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7837d6a8404c448a969938e21c1b1d8e
Source dataset
uspto-grants-1986_12
Patent number
US04627872

Reaction notes

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