2-Propanesulfonyl chloride → Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-yl ester

HRID 48458Notes

Reaction equation

HRID 48458 reaction equation
CC([O-])(C)C.[K+].[NH2:7][C:8]1[N:13]=[C:12]([NH2:14])[C:11]([CH2:15][C:16]2[CH:17]=[C:18]([OH:26])[C:19]3[CH:20]=[CH:21][N:22]([CH3:25])[C:23]=3[CH:24]=2)=[CH:10][N:9]=1.[CH3:27][CH:28]([S:30](Cl)(=[O:32])=[O:31])[CH3:29]>CN(C)C=O>[NH2:7][C:8]1[N:13]=[C:12]([NH2:14])[C:11]([CH2:15][C:16]2[CH:24]=[C:23]3[C:19]([CH:20]=[CH:21][N:22]3[CH3:25])=[C:18]([O:26][S:30]([CH:28]([CH3:29])[CH3:27])(=[O:32])=[O:31])[CH:17]=2)=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 824082-Propanesulfonyl chlorideHCID 227428906-(2,4-Diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 86759375Propane-2-sulfonic acid 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-yl esterYield 37.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butylate (150 mg, 1.31 mmol) was added at 0° C. (ice bath) to a solution of 6-(2,4-diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-ol (Example 4; 293 mg, 1.09 mmol) in N,N-dimethylformamide (33 mL). After 30 min the solution was treated with propane-2-sulfonyl chloride (190 mg, 1.31 mmol), and the ice bath was removed. After 2.5 h the reaction mixture was poured into ice water, set to pH 9-10 with 25% aqueous ammonia solution, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried (MgSO4), and evaporated. Column chromatography (SiO2; CH2Cl2/MeOH/NH4OH19:1:0.05) afforded the title compound (153 mg, 37%). White solid.

Workup

  1. customthe ice bath was removed
  2. additionAfter 2.5 h the reaction mixture was poured into ice water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-f70a69f9a0aa4bd8a59d473235e658e6
Source dataset
uspto-grants-2004_03
Patent number
US06703397B2

Reaction notes

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