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

HRID 2249989Notes

Reaction equation

HRID 2249989 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 recrystalized 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, 3), 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. customrecrystalized from EtOAc (15 mL)

Sources & evidence

ORD record
ord-f19fbfe4bcc1448595c05d3b3dd05036
Source dataset
uspto-grants-2008_01
Patent number
US07314934B2

Reaction notes

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