3-Methoxypropylamine → 4,6-Dichloro-N-(3-methoxypropyl)pyrimidin-2-amine

HRID 1248885Notes

Reaction equation

HRID 1248885 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].Cl[C:8]1[N:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[N:9]=1>O1CCCC1>[Cl:15][C:10]1[CH:11]=[C:12]([Cl:14])[N:13]=[C:8]([NH:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[N:9]=1

Participants

4

Reactant 2

HCID 16723-MethoxypropylamineHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 136496914,6-Dichloro-N-(3-methoxypropyl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

48 g (0.54 mole) of 3-methoxypropylamine are added dropwise to 50 g (0.27 mole) of 2,4,6-trichloropyrimidine, dissolved in 300 ml of tetrahydrofuran, at -30° C. After the reaction mixture has thawed to room temperature and been stirred for a further six hours, it is poured into ice water and extracted with methylene chloride, the extract is dried over sodium sulphate and the solvent is removed. The resulting residue is subjected to steam distillation in the course of which 10.6 g (16.6% of theory) of the desired pyrimidine pass over as a solid, melting point 48° C.

Workup

  1. customhas thawed to room temperature
  2. extractionextracted with methylene chloride
  3. dry with materialthe extract is dried over sodium sulphate
  4. customthe solvent is removed
  5. distillationThe resulting residue is subjected to steam distillation in the course of which 10.6 g (16.6% of theory) of the desired pyrimidine pass over as a solid, melting point 48° C.

Sources & evidence

ORD record
ord-2f1d646afc524ab9942ddc9a13be653d
Source dataset
uspto-grants-1986_12
Patent number
US04627872

Reaction notes

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