Hydrazine hydrate (1:1) → 6-{[(2-Amino-1,3-thiazol-4-yl)methyl]amino}-5-fluoro-4-hydrazino-2-methylpyrimidine

HRID 1366490Notes

Reaction equation

HRID 1366490 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][NH:8][C:9]2[C:14]([F:15])=[C:13](Cl)[N:12]=[C:11]([CH3:17])[N:10]=2)[N:6]=1.O.[NH2:19][NH2:20]>CS(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][NH:8][C:9]2[N:10]=[C:11]([CH3:17])[N:12]=[C:13]([NH:19][NH2:20])[C:14]=2[F:15])[N:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86636959N-[(2-amino-1,3-thiazol-4-yl)methyl]-6-chloro-5-fluoro-2-methyl-4-pyrimidinamine

Product 1

HCID 866369606-{[(2-Amino-1,3-thiazol-4-yl)methyl]amino}-5-fluoro-4-hydrazino-2-methylpyrimidineYield 28%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-[(2-Amino-1,3-thiazol-4-yl)methyl]-6-chloro-5-fluoro-2-methyl-4-pyrimidinamine (450 mg, 1.56 mmol) was dissolved in 5 ml of DMSO and 5 ml of hydrazine monohydrate was added. The mixture was stirred overnight and was purified by RP-HPLC to provide 6-{[(2-amino-1,3-thiazol-4-yl)methyl]amino}-5-fluoro-4-hydrazino-2-methylpyrimidine (125 mg, 28%). LCMS: (M+H)+: 284.1.

Workup

  1. customwas purified by RP-HPLC

Sources & evidence

ORD record
ord-0ee3246e16784d86af63bd9885398327
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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