Triethylamine → 2,4-Dichloro-5-fluoro-6-hydrazinopyrimidine

HRID 1366712Notes

Reaction equation

HRID 1366712 reaction equation
O.[NH2:2][NH2:3].C(N(CC)CC)C.[Cl:11][C:12]1[N:17]=[C:16]([Cl:18])[C:15]([F:19])=[C:14](Cl)[N:13]=1>CO>[Cl:11][C:12]1[N:17]=[C:16]([Cl:18])[C:15]([F:19])=[C:14]([NH:2][NH2:3])[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 133889932,4,6-Trichloro-5-fluoropyrimidine

Product 1

HCID 866370372,4-Dichloro-5-fluoro-6-hydrazinopyrimidineYield 36.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To hydrazine monohydrate (289 μL, 5.96 mmol) and triethylamine (830 μL, 5.96 mmol) in MeOH (15 mL) was added a solution of 2,4,6-trichloro-5-fluoropyrimidine (1.0 g, 4.96 mmol) in MeOH (15 mL), and the mixture was stirred overnight. When the reaction was complete as determined by LCMS, the solution was concentrated in vacuo, and the resulting crude product was purified by RP-HPLC to provide 2,4-dichloro-5-fluoro-6-hydrazinopyrimidine (358 mg, 32%). LCMS: (M+H)+: 196.9.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customthe resulting crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-e6dcbc17bc6e42d09e64e04251bac490
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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