Benzylamine → 4-N-benzyl-6-chloropyrimidine-2,4-diamine

HRID 1838964Notes

Reaction equation

HRID 1838964 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:1][C:2]1[N:3]=[C:4]([Cl:9])[CH:5]=[C:6]([NH:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 14842704-N-benzyl-6-chloropyrimidine-2,4-diamineYield 50.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4,6-dichloropyrimidine (0.5 g, 3.05 mmol), benzylamine (0.35 ml, 3.2 mmol), potassium carbonate (0.25 g, 1.81 mmol) and ethanol (15 ml) were heated to reflux for 16 h. The reaction mixture was cooled to room temperature and the solvents were removed under reduced pressure. The residue was triturated with ethyl acetate and the white product was collected by filtration. Concentration of the ethyl acetate filtrate also afforded a second crop of product. The combined solids were dried to give the required pyrimidine (0.36 g, 50%), m.p. 136° C.; δH (200 MHz, d6-DMSO) 4.55 (2H, br s, OCH2), 5.87 (1H, br s, C(5)H), 6.54 (2H, br s, NH2), 7.35-7.41 (5H, m, C6H5), 7.72 (1H, m, NH); m/z (+EI) 234 (M+, 85%), 106 (100), 91 (C6H5CH2+, 51%).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 16 h
  3. customthe solvents were removed under reduced pressure
  4. customThe residue was triturated with ethyl acetate
  5. filtrationthe white product was collected by filtration
  6. customConcentration of the ethyl acetate filtrate also afforded a second crop of product
  7. customThe combined solids were dried

Sources & evidence

ORD record
ord-858455cc353b4e928daddf56208e776a
Source dataset
uspto-grants-2004_01
Patent number
US06677345B1

Reaction notes

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