4,6-Dichloro-5-(2-methoxyphenoxy)-2-(pyridin-4-YL)pyrimidine → 2-Phenyl-ethanesulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide

HRID 8602

Reaction equation

HRID 8602 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH: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>CN(C=O)C>[Cl:17][C:6]1[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH: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]=[CH:11][C:10]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 111754584,6-Dichloro-5-(2-methoxyphenoxy)-2-(pyridin-4-YL)pyrimidineHCID 688981502-Phenyl-ethanesulfonic acid amide potassium salt

Product 1

HCID 865924712-Phenyl-ethanesulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amideYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4,6-dichloro-5-(2-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (2 g) and 2-phenyl-ethanesulfonic acid amide potassium salt (2.82 g, Referential Example 1e) in DMF (50 ml) was stirred at rt for 16 h. Bulk of the solvent was evaporated before it was diluted with diethyl ether (50 ml). The mixture was acidified with 10% aq. citric acid. The precipitate that formed was collected, washed with diethyl ether (100 ml) and dried to give 2-phenyl-ethanesulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide (2.23 g) as a beige powder. LC-MS: tR=4.93 min, [M+1]+=497.22, [M−1]−=494.96.

Workup

  1. customBulk of the solvent was evaporated before it
  2. additionwas diluted with diethyl ether (50 ml)
  3. customThe precipitate that formed
  4. customwas collected
  5. washwashed with diethyl ether (100 ml)
  6. customdried

Sources & evidence

ORD record
ord-50ab374672784712afdda58eb7ef9ef4
Source dataset
uspto-grants-2006_08
Patent number
US07091201B2

Linked notes

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