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

HRID 2357206Notes

Reaction equation

HRID 2357206 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-fa9b15e5e3b944a89efb5c7a1ec76202
Source dataset
uspto-grants-2010_07
Patent number
US07759486B2

Reaction notes

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