Sodium Bicarbonate → (6-Chloro-2-methoxy-pyrimidin-4-yl)-(2,2-difluoro-2-phenyl-ethyl)-amine

HRID 216202Notes

Reaction equation

HRID 216202 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[F:11][C:12]([F:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:13][NH2:14].C([O-])(O)=O.[Na+]>CCO.O>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH3:10])[N:3]=[C:2]([NH:14][CH2:13][C:12]([F:11])([F:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 120521604,6-Dichloro-2-methoxypyrimidineHCID 126355292,2-Difluoro-2-phenylethylamine

Product 1

HCID 86240121(6-Chloro-2-methoxy-pyrimidin-4-yl)-(2,2-difluoro-2-phenyl-ethyl)-amineYield 52.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4,6-dichloro-2-methoxy-pyrimidine (0.66 g, 3.69 mmol), 2,2-difluoro-2-phenyl-ethylamine (0.58 g, 3.69 mmol), and NaHCO3 (0.93 g, 11.1 mmol) in 95% EtOH (10 mL) is heated to reflux. After stirred at 85° C. for 5 h. The mixture is diluted with water, filtered, washed (water), and dried to afford (6-chloro-2-methoxy-pyrimidin-4-yl)-(2,2-difluoro-2-phenyl-ethyl)-amine as a solid (0.58 g). LCMS: RT=3.17 minutes, MS: 300 (M+H). 1H NMR (300 MHz, CDCl3) □7.57-7.45 (5H, m), 6.1 (1H, s), 5.2 (1H, s), 4.2-4 (2H, m), 3.92 (3H, s).

Workup

  1. temperatureis heated to reflux
  2. filtrationfiltered
  3. washwashed (water)
  4. customdried

Sources & evidence

ORD record
ord-518feff110fb43fa9a5fc66f252dc7a1
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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