Triethylamine → 5-Fluoro-4-hydrazino-2-methyl-6-[(1,3-thiazol-2-ylmethyl)amino]pyrimidine

HRID 1366468Notes

Reaction equation

HRID 1366468 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6](Cl)[N:5]=[C:4]([CH3:10])[N:3]=1.[S:11]1[CH:15]=[CH:14][N:13]=[C:12]1[CH2:16][NH2:17].C(N(CC)CC)C.[NH2:25][NH2:26]>CS(C)=O>[F:8][C:7]1[C:2]([NH:25][NH2:26])=[N:3][C:4]([CH3:10])=[N:5][C:6]=1[NH:17][CH2:16][C:12]1[S:11][CH:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9321HydrazineHCID 27565071,3-Thiazol-2-ylmethanamineHCID 137310334,6-Dichloro-5-fluoro-2-methylpyrimidine

Product 1

HCID 669358995-Fluoro-4-hydrazino-2-methyl-6-[(1,3-thiazol-2-ylmethyl)amino]pyrimidineYield 38%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4,6-Dichloro-5-fluoro-2-methylpyrimidine (180 mg, 1 mmol) was dissolved in 1 mL of DMSO and stirred at room temperature. (1,3-Thiazol-2-ylmethyl)amine (124 mg, 1.1 mmol) was added, followed by triethylamine (150 μL, 1.1 mmol). The resulting reaction mixture was stirred for 3 h, then hydrazine was added (1.0 mL), and the contents were heated to 60° C. for 1.5 h. The reaction mixture was then cooled to room temperature and purified by RP-HPLC to provide 5-fluoro-4-hydrazino-2-methyl-6-[(1,3-thiazol-2-ylmethyl)amino]pyrimidine (97 mg, 38%). LCMS: (M+H)+: 255.2.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 3 h
  3. temperaturethe contents were heated to 60° C. for 1.5 h
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-d46d5a7c1e3a46f6a58f781c39cca55f
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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