Methylamine → 6-(Methylamino)pyrimidine-4-carbonitrile

HRID 2247240Notes

Reaction equation

HRID 2247240 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.[CH3:10][NH2:11]>C1COCC1>[CH3:10][NH:11][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 224988816-Chloropyrimidine-4-carbonitrile

Product 1

HCID 224988766-(Methylamino)pyrimidine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-chloro-pyrimidine-4-carbonitrile (1.37 g, 9.84 mmol) stirring in 10 ml THF under N2 was added a methylamine solution (2.0 M in THF, Aldrich) in aliquots, causing immediate precipitation. Reaction progress was monitored after addition of 5 ml methylamine solution, then 3 ml, then 2 ml. The mixture was concentrated and filtered through a pad of silica, eluting with 2%->5% MeOH in CH2Cl2 to obtain 6-methylamino-pyrimidine-4-carbonitrile as a pale yellow solid. MS: 135.0 (M+1); Calc'd. for C6H6N4—134.14.

Workup

  1. customprecipitation
  2. customReaction progress
  3. concentrationThe mixture was concentrated
  4. filtrationfiltered through a pad of silica
  5. washeluting with 2%->5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-4f5d06d92d9a4d51b96ad4b733a270bb
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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