Hydrochloric Acid → 2-chloro-5-fluoro-6-hydrazino-N-methyl-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine

HRID 1366606Notes

Reaction equation

HRID 1366606 reaction equation
CC(OC([N:8](C(OC(C)(C)C)=O)[N:9]([C:17]1[C:22]([F:23])=[C:21]([N:24]([CH3:31])[CH2:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)[N:20]=[C:19]([Cl:32])[N:18]=1)C(OC(C)(C)C)=O)=O)(C)C.Cl>CO>[Cl:32][C:19]1[N:20]=[C:21]([N:24]([CH3:31])[CH2:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)[C:22]([F:23])=[C:17]([NH:9][NH2:8])[N:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86637002Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[methyl(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate

Product 1

HCID 866370032-chloro-5-fluoro-6-hydrazino-N-methyl-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tris(1,1-dimethylethyl)2-{2-chloro-5-fluoro-6-[methyl (1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate (1.51 g, 2.57 mmol) was dissolved in MeOH (25 mL) and HCl (4M in 1,4-dioxane) (25 mL) at room temperature. The reaction mixture was left to stir over 4 days and then evaporated to provide 2-chloro-5-fluoro-6-hydrazino-N-methyl-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine, assumed dihydrochloride, as a beige solid (0.9034 g, 98%). LCMS: (M+H−2HCl)+=289.0.

Workup

  1. customat room temperature
  2. waitThe reaction mixture was left
  3. customevaporated

Sources & evidence

ORD record
ord-bafbad146b5f4a76866b303fd32861ca
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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