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

HRID 524043

Reaction equation

HRID 524043 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.[CH:12]([N:15](C(C)C)CC)(C)C.CN>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:15][CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 71472322-chloro-N-methyl-5-nitropyrimidin-4-amineYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-dichloro-5-nitropyrimidine (5 g, 26 mmol) in THF (50 mL) was added diisopropylethylamine (3.36 g, 26 mmol) at −78° C., followed by the dropwise addition of methylamine (13 mL, 2 mol/L in methanol, 26 mmol). After the addition, the mixture was warmed to RT and stirred for 3 h. The reaction mixture was then diluted with ethyl acetate and washed with brine (50 mL*3). The organic layer was dried over sodium sulfate, filtered and concentrated to give the title compound (4.4 g, 100%) as a yellow solid. MS (ES+) C5H5ClN4O2 requires: 188, 190. found: 189, 191 [M+H]+.

Workup

  1. additionAfter the addition
  2. washwashed with brine (50 mL*3)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0743059575294e81abd40c482cef0bd1
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Linked notes

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