Hydrazine hydrate (1:1) → 5-fluoro-6-hydrazino-N-methyl-2-(methylthio)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine

HRID 1366631Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([N:10]([CH3:17])[CH2:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[C:3]=1[F:18].O.[NH2:20][NH2:21]>CS(C)=O>[F:18][C:3]1[C:4]([N:10]([CH3:17])[CH2:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[N:5][C:6]([S:8][CH3:9])=[N:7][C:2]=1[NH:20][NH2:21]

Participants

Conditions

Temperature: 80 °C

Procedure

6-Chloro-5-fluoro-N-methyl-2-(methylthio)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine (0.4928 g, 1.621 mmol) was dissolved in 5 mL of DMSO and hydrazine monohydrate (0.63 mL, 12.96 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-6-hydrazino-N-methyl-2-(methylthio)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine as a beige solid (0.2112 g, 43%). LCMS: (M+H)+=301.0.

Workup

customsealed
customThe reaction mixture was purified by RP-HPLC

Sources & evidence

ORD record: ord-4384270f64934887a6fc5f0b91cf3270
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

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