Methylamine → 2-chloro-N-methyl-5-nitropyrimidin-4-amine

HRID 29818

Reaction equation

HRID 29818 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][NH2:13]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:13][CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 71472322-chloro-N-methyl-5-nitropyrimidin-4-amineYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4-dichloro-5-nitropyrimidine (7.26 g, 37.4 mmol) in THF (100 ml) is cooled to −78° C. A solution of methyl amine (8 M in methanol, 9.35 mL, 74.8 mmol) is added dropwise. The mixture is allowed to warm to room temperature, and concentrated. The residue is partitioned between ethyl acetate and water. The layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated to afford the title product (7.0 g). (Note: the product contains 5% regio-isomer, 4-chloro-2-(methylamino)-5-nitropyrimidine). The residue is used in the next step without further purification.

Workup

  1. concentrationconcentrated
  2. customThe residue is partitioned between ethyl acetate and water
  3. customThe layer is separated
  4. extractionthe aqueous layer is extracted with ethyl acetate
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-83d91350d3d04fa4bc5182a219334930
Source dataset
uspto-grants-2008_09
Patent number
US07423038B2

Linked notes

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