Phosphorus oxychloride → 5-Benzyl-4-chloro-6-methylpyrimidin-2-amine

HRID 989724

Reaction equation

HRID 989724 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([CH3:16])[N:3]=1.P(Cl)(Cl)([Cl:19])=O>>[CH2:9]([C:5]1[C:6]([Cl:19])=[N:7][C:2]([NH2:1])=[N:3][C:4]=1[CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178433370HCID 178433370, compound

Product 1

HCID 8202385-Benzyl-4-chloro-6-methylpyrimidin-2-amineYield 53.7%

Conditions

Temperature
90 °C

Procedure

A mixture of 2-amino-5-benzyl-6-methylpyrimidine-4-ol (1.2 g, 5.57 mmol) and phosphorous oxychloride (9 ml) was kept to warm at 90° C. for 6 hours. The reaction mixture was concentrated in vacuo. Ice-water was added to the residue and an aqueous ammonia was cautiously added thereto. The solution was extracted with chloroform. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (chloroform: ethyl acetate=8:2) to give the object compound (700 mg, 53.7%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionIce-water was added to the residue
  3. additionan aqueous ammonia was cautiously added
  4. extractionThe solution was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (chloroform: ethyl acetate=8:2)

Sources & evidence

ORD record
ord-c02623ac7a9d416687320c99da6f9f30
Source dataset
uspto-grants-2002_10
Patent number
US06458798B1

Linked notes

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