Hydrazine hydrate (1:1) → 1-(2-Chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-3-methyl-3-pyrrolidinol

HRID 1366522Notes

Reaction equation

HRID 1366522 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C:10]([CH3:14])([OH:13])[CH2:9]2)[C:5]([F:15])=[C:4](Cl)[N:3]=1.O.[NH2:18][NH2:19]>CS(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C:10]([CH3:14])([OH:13])[CH2:9]2)[C:5]([F:15])=[C:4]([NH:18][NH2:19])[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866369741-(2,6-Dichloro-5-fluoro-4-pyrimidinyl)-3-methyl-3-pyrrolidinol

Product 1

HCID 866369751-(2-Chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-3-methyl-3-pyrrolidinolYield 21.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-(2,6-Dichloro-5-fluoro-4-pyrimidinyl)-3-methyl-3-pyrrolidinol (0.486 g, 1.83 mmol) and hydrazine monohydrate (0.53 mL, 10.96 mmol) in DMSO (5 mL) were heated at 50° C. until the reaction was deemed complete. Purification by RP-HPLC provided 1-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-3-methyl-3-pyrrolidinol as a brown solid (0.104 g, 21%). LCMS: (M+H)+=262.1.

Workup

  1. customPurification by RP-HPLC

Sources & evidence

ORD record
ord-2dd91fa7d45c4610b6157d339999f2a0
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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