2-Propanesulfonyl chloride → Propane-2-sulphonic acid 5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-ethoxy-2-(6-methyl-pyridin-3-yl)-phenyl ester

HRID 2416325Notes

Reaction equation

HRID 2416325 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([OH:20])[C:18]=1I)[CH2:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)[CH3:2].C[C:22]([O-])([CH3:24])[CH3:23].[K+].[CH3:27][CH:28]([S:30](Cl)(=[O:32])=[O:31])[CH3:29]>CN(C)C=O>[NH2:14][C:11]1[N:10]=[C:9]([NH2:15])[C:8]([CH2:7][C:6]2[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:18]([C:8]3[CH:9]=[N:10][C:22]([CH3:23])=[CH:24][CH:7]=3)=[C:17]([O:20][S:30]([CH:28]([CH3:29])[CH3:27])(=[O:32])=[O:31])[CH:16]=2)=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 824082-Propanesulfonyl chlorideHCID 226368575-(3-Ethoxy-5-hydroxy-4-iodo-benzyl)-pyrimidine-2,4-diamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 17937371Propane-2-sulphonic acid 5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-ethoxy-2-(6-methyl-pyridin-3-yl)-phenyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(3-Ethoxy-5-hydroxy-4-iodo-benzyl)-pyrimidine-2,4-diamine (see example 32 stage a)) (5.9 g; 15.28 mmol) is dissolved in dimethylformamide (150 ml), and potassium tert-butylate (2.57 g; 22.92 mmol) is added. Propane-2-sulphonyl chloride (2.56 ml; 22.92 mmol) is added at 0° C. The mixture is then stirred for one hour at room temperature. The reaction mixture is evaporated and the residue is chromatographed over silica gel with methylene chloride/methanol (19/1) and 0.5% ammonia. The pure fractions are combined and the solvent is evaporated off.

Workup

  1. customThe reaction mixture is evaporated
  2. customthe residue is chromatographed over silica gel with methylene chloride/methanol (19/1) and 0.5% ammonia
  3. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-44a2ce4b3ee742138e06dd792fdc69ff
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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