2,4-Dichloro-5-cyanopyrimidine → 2-Amino-4-chloropyrimidine-5-carbonitrile

HRID 243184Notes

Reaction equation

HRID 243184 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[CH:4][N:3]=1.[NH3:11].CO>CO>[NH2:11][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 140269072,4-Dichloro-5-cyanopyrimidineHCID 21705897Ammonia methanol

Product 1

HCID 717413792-Amino-4-chloropyrimidine-5-carbonitrileYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2,4-dichloropyrimidine-5-carbonitrile (500 mg, 2.87 mmol) in MeOH (5 mL) was added 2M NH3/MeOH (5 mL). After stirring for 20 min the resulting precipitate was filtered and washed with MeOH to afford the title compound as a white solid (173 mg, 39%). LCMS (Method C): RT 1.91 min [M+H]+ 155.1. 1H NMR (DMSO-d6, 400 MHz): δ 8.68 (1H, s), 8.23 (2H, br s)

Workup

  1. filtrationwas filtered
  2. washwashed with MeOH

Sources & evidence

ORD record
ord-63337abefb2e42b79d8a45088de999e1
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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