Triethylamine → 2-Pyridin-2-yl-ethanesulfonic acid [6-chloro-5-(2-methoxyphenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide

HRID 8614Notes

Reaction equation

HRID 8614 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].[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][CH2:32][S:33]([NH2:36])(=[O:35])=[O:34].C(N(CC)CC)C>CS(C)=O.C(OCC)(=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:26]2[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=2)(=[O:35])=[O:34])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 111754584,6-Dichloro-5-(2-methoxyphenoxy)-2-(pyridin-4-YL)pyrimidineHCID 68897963HCID 68897963, compound

Product 1

HCID 865924742-Pyridin-2-yl-ethanesulfonic acid [6-chloro-5-(2-methoxyphenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amideYield 38%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,6-dichloro-5-(2-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (1.75 g, Referential Example 7) and 2-pyridin-2-yl-ethanesulfonic acid amide potassium salt (1.13 g) in DMSO (30 ml) was stirred at rt for 24 h. Triethylamine (657 mg) was added and stirring was continued for another 96 h before the mixture was diluted with ethyl acetate (150 ml) and washed 4% aq. citric acid and water. The aqueous phase was extracted three more times with EA. The organic phase was dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel eluting with EA containing 0–10% methanol to give 2-pyridin-2-yl-ethanesulfonic acid [6-chloro-5-(2-methoxyphenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide (950 mg) as a brown powder. LC-MS: tR=3.63 min, [M+1]+=498.31, [M−1]−=496.10.

Workup

  1. washwashed 4% aq. citric acid and water
  2. extractionThe aqueous phase was extracted three more times with EA
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated
  5. customThe crude product was purified by column chromatography on silica gel eluting with EA containing 0–10% methanol

Sources & evidence

ORD record
ord-42c3a2963f314b3f80a28108b2f9c847
Source dataset
uspto-grants-2006_08
Patent number
US07091201B2

Reaction notes

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