2-(3-Amino-phenylmethanesulfonyl)-ethanol → 2-{3-[4-(2-Methoxy-phenyl)-pyrimidin-2-ylamino]-phenylmethanesulfonyl}-ethanol

HRID 2088725Notes

Reaction equation

HRID 2088725 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9]([CH2:12][CH2:13][OH:14])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl[C:16]1[N:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])[CH:19]=[CH:18][N:17]=1>CN(C=O)C>[CH3:29][O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:20]1[CH:19]=[CH:18][N:17]=[C:16]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][S:9]([CH2:12][CH2:13][OH:14])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=2)[N:21]=1

Participants

4

Reactant 2

HCID 153460102-(3-Amino-phenylmethanesulfonyl)-ethanolHCID 249018822-Chloro-4-(2-methoxyphenyl)pyrimidine

Product 1

HCID 251017352-{3-[4-(2-Methoxy-phenyl)-pyrimidin-2-ylamino]-phenylmethanesulfonyl}-ethanolYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(3-amino-phenylmethanesulfonyl)-ethanol (0.215 g, 1 mmol) and 2-chloro-4-(2-methoxy-phenyl)-pyrimidine (0.22 g, 1 mmol) in DMF (3 mL) was stirred for 2 hours at 80° C. (TLC control). The solvent was removed under reduced pressure to afford an oily residue which was crystallized from isopropanol yielding 2-{3-[4-(2-methoxy-phenyl)-pyrimidin-2-ylamino]-phenylmethanesulfonyl}-ethanol (0.3 g, 75%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto afford an oily residue which
  3. customwas crystallized from isopropanol

Sources & evidence

ORD record
ord-0977b85a8d284556bdb56f32f68ff942
Source dataset
uspto-grants-2013_05
Patent number
US08436007B2

Reaction notes

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