Hydrazine hydrate (1:1) → 2-chloro-5-fluoro-6-hydrazino-N-methyl-N-(4-pyridinylmethyl)-4-pyrimidinamine

HRID 1366518Notes

Reaction equation

HRID 1366518 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:16])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:5]([F:17])=[C:4](Cl)[N:3]=1.O.[NH2:20][NH2:21]>CS(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:16])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:5]([F:17])=[C:4]([NH:20][NH2:21])[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866369712,6-dichloro-5-fluoro-N-methyl-N-(4-pyridinylmethyl)-4-pyrimidinamine

Product 1

HCID 866369722-chloro-5-fluoro-6-hydrazino-N-methyl-N-(4-pyridinylmethyl)-4-pyrimidinamineYield 23.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

2,6-Dichloro-5-fluoro-N-methyl-N-(4-pyridinylmethyl)-4-pyrimidinamine (0.3516 g, 1.23 mmol) was dissolved in 5 mL of DMSO and hydrazine monohydrate (0.36 mL, 7.4229 mmol). The reaction vessel was pressure sealed and heated to 50° C. for 2.5 hours. The reaction mixture was then purified by RP-HPLC to provide 2-chloro-5-fluoro-6-hydrazino-N-methyl-N-(4-pyridinylmethyl)-4-pyrimidinamine as a wine colored solid (0.0803 g, 23%). LCMS: (M+H)+=283.0.

Workup

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

Sources & evidence

ORD record
ord-6f72e14c3fd243969eac7a9af9d6d0af
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…