Sodium Bicarbonate → (6-Chloro-2-methoxy-pyrimidin-4-yl)-[2-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-ethyl]-amine

HRID 216172Notes

Reaction equation

HRID 216172 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.Cl.[F:12][C:13]1([F:25])[O:17][C:16]2[CH:18]=[CH:19][C:20]([CH2:22][CH2:23][NH2:24])=[CH:21][C:15]=2[O:14]1.C(=O)(O)[O-].[Na+]>CCO>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH3:10])[N:3]=[C:2]([NH:24][CH2:23][CH2:22][C:20]2[CH:19]=[CH:18][C:16]3[O:17][C:13]([F:25])([F:12])[O:14][C:15]=3[CH:21]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 120521604,6-Dichloro-2-methoxypyrimidine2×HCID 690734742-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-ethylamine hydrochloride2×

Product 1

HCID 57636005(6-Chloro-2-methoxy-pyrimidin-4-yl)-[2-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-ethyl]-amineYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4,6-dichloro-2-methoxy-pyrimidine (0.606 g, 3.38 mmol, Intermediate (4)] and 2-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-ethylamine hydrochloride (0.884 g, 3.72 mmol, Intermediate (62)]) in EtOH (11 mL) is added sodium bicarbonate (0.85 g, 10.14 mmol) and heated to reflux for 4 hours. The reaction mixture is filtered and filtrate is concentrated, residue solid is washed with small amount of EtOH to yield (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-ethyl]-amine [0.918 g, 79%, Intermediate (63)] as a solid. LC/MS: MS: 344 (M+H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. filtrationThe reaction mixture is filtered
  4. concentrationfiltrate is concentrated
  5. washresidue solid is washed with small amount of EtOH

Sources & evidence

ORD record
ord-d1518d867434477c83ec8be417a47fd3
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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