4-[4,6-Dichloro-5-(3-methoxy-phenoxy)-pyrimidin-2-yl]-morpholine → 2-Phenyl-ethanesulfonic acid [6-chloro-5-(3-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl]-amide

HRID 8607

Reaction equation

HRID 8607 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[C:6]([Cl:17])[N:5]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:3]=1.[K].[C:25]1([CH2:31][CH2:32][S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CS(C)=O.O>[Cl:17][C:6]1[N:5]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:3]=[C:2]([NH:36][S:33]([CH2:32][CH2:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:34])=[O:35])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1

Participants

5

Reactant 2

HCID 219837204-[4,6-Dichloro-5-(3-methoxy-phenoxy)-pyrimidin-2-yl]-morpholineHCID 688981502-Phenyl-ethanesulfonic acid amide potassium salt

Product 1

HCID 865924722-Phenyl-ethanesulfonic acid [6-chloro-5-(3-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl]-amideYield 90.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 4-[4,6-dichloro-5-(3-methoxy-phenoxy)-pyrimidin-2-yl]-morpholine (1.0 g) and 2-phenyl-ethanesulfonic acid amide potassium salt (1.57 g, Referential Example 1e) in DMSO (15 ml) was stirred at 60° C. for 24 h. The solution was diluted with water (75 ml) and extracted twice with diethyl ether (75 ml) before it was acidified with 10% aq. citric acid. The mixture was extracted twice with EA (150 ml). The organic phase was washed with water (50 ml). The product precipitated upon evaporation of the solvent. The solid was collected, washed with diethyl ether and dried to give 2-phenyl-ethanesulfonic acid [6-chloro-5-(3-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl]-amide (1.28 g) as off-white powder. LC-MS: tR=5.34 min, [M+1]+=505.12, [M−1]−=502.97.

Workup

  1. extractionextracted twice with diethyl ether (75 ml) before it
  2. extractionThe mixture was extracted twice with EA (150 ml)
  3. washThe organic phase was washed with water (50 ml)
  4. customThe product precipitated upon evaporation of the solvent
  5. customThe solid was collected
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-50b2dcef9ed84e548750be65d0cf0b62
Source dataset
uspto-grants-2006_08
Patent number
US07091201B2

Linked notes

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