Hydrazine hydrate (1:1) → HCID 67327558, compound

HRID 1774550Notes

Reaction equation

HRID 1774550 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([O:10][C:11]2[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][CH:12]=2)[CH:3]=1.O.[NH2:22][NH2:23]>CO>[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([O:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([NH:22][NH2:23])=[O:16])=[CH:13][CH:12]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67328692HCID 67328692, compound2×

Product 1

HCID 67327558HCID 67327558, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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-736ddc18354643c687c0181657a2f2d3
Source dataset
uspto-grants-2016_02
Patent number
US09260417B2

Reaction notes

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