Ammonia → 4-Amino-6-chloro-2-methylthiopyrimidine

HRID 1774549Notes

Reaction equation

HRID 1774549 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[NH3:11]>C1COCC1>[NH2:11][C:6]1[CH:7]=[C:2]([Cl:1])[N:3]=[C:4]([S:9][CH3:10])[N:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 805314,6-Dichloro-2-(methylthio)pyrimidine

Product 1

HCID 704964-Amino-6-chloro-2-methylthiopyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 6 was prepared from commercially available 4,6-dichloro-2-(methylthio)pyrimidine followed scheme 4. To prepare compound 6.1,4,6-Dichloro-2-(methylthio)pyrimidine was reacted with ammonia in THF in a sealed tube to provide 4-Amino-6-chloro-2-(methylthio)pyrimidine in good yield. Amino group of the resulting compound was protected with suitable protecting group such as BOC to afford compound 6.1. Compound 6.1 was then reacted with methyl 4-hydroxybenzoate in the presence of base to provide the amine protected intermediate, 2 which upon deprotection under acidic condition to afford methyl 4-(6-amino-2-(methylthio)pyrimidin-4-yloxy)benzoate (3). Reaction of compound 3 with hydrazine hydrate in methanol provided 4-(6-amino-2-(methylthio)pyrimidin-4-yloxy)benzohydrazide (6.4) in good yield. The hydrazide was then reacted with S-methyl N-[3-(trifluoromethyl-phenyl)thiourea in the presence of base to yield compound 6.

Sources & evidence

ORD record
ord-4c058be6e3a24f92808c311563a556ce
Source dataset
uspto-grants-2016_02
Patent number
US09260417B2

Reaction notes

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