Hydrazine hydrate (1:1) → HCID 178503508, compound

HRID 1366633Notes

Reaction equation

HRID 1366633 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][CH2:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[C:3]=1[F:17].O.[NH2:19][NH2:20]>CS(C)=O>[F:17][C:3]1[C:2](=[N:19][NH2:20])[N:7]=[C:6]([S:8][CH3:9])[NH:5][C:4]=1[NH:10][CH2:11][C:12]1[S:13][CH:14]=[CH:15][N:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866370136-chloro-5-fluoro-2-(methylthio)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine

Product 1

HCID 178503508HCID 178503508, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

6-Chloro-5-fluoro-2-(methylthio)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine (0.6773 g, 2.336 mmol) was dissolved in DMSO (7 mL) and hydrazine monohydrate (0.91 mL, 18.72 mmol). The reaction vessel was pressure sealed and heated to 80° C. for 2 hours. The reaction mixture was purified by RP-HPLC to provide 5-fluoro-2-(methylthio)-6-[(1,3-thiazol-2-ylmethyl)amino]-4(1H)-pyrimidinone hydrazone as an orange solid (0.1958 g, 29%). LCMS: (M+H)+=287.1.

Workup

  1. customsealed
  2. customThe reaction mixture was purified by RP-HPLC

Sources & evidence

ORD record
ord-f5e59e9aa8d24c4fbcb1c37487814dd7
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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