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

HRID 2249724Notes

Reaction equation

HRID 2249724 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, 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. customrecrystalized from EtOAc (15 mL)

Sources & evidence

ORD record
ord-02d1490999884ef5852c74aa85918c73
Source dataset
uspto-grants-2008_01
Patent number
US07314881B2

Reaction notes

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