Ammonia → 4-Amino-6-chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

HRID 556536Notes

Reaction equation

HRID 556536 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6](Cl)[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[NH3:13]>C1C=CC=CC=1>[NH2:13][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([Cl:1])[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

Product 1

HCID 98557864-Amino-6-chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To the solution of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (2 g, 7.36 mmol) in benzene (20 mL) was introduced NH3 gas for 30 minutes (hereinafter “min”). The formed solid was then filtered and recrystallized from EtOAc (15 mL) to give 1.18 g (80%) of pure 4-amino-6-chloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde. 1H-NMR: δ 2.50 (s, 3H), 7.28 (t, 3H, J=45 Hz, D2O exchangeable), 8.65 (d, 3H, J=41 Hz, D2O exchangeable), 10.11 (s, 1H).

Workup

  1. filtrationThe formed solid was then filtered
  2. customrecrystallized from EtOAc (15 mL)

Sources & evidence

ORD record
ord-cb82edca50734d53b8d3b303418edf65
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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