Dimethyl Sulfoxide → 1-Propyl-8-(1H-pyrazol-4-yl)-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one

HRID 925553Notes

Reaction equation

HRID 925553 reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]2[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20]3[C:19](=[O:30])[N:18]([CH2:31][CH2:32][CH3:33])[C:17]([N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[N:16][C:15]=3[N:14]=2)[CH:10]=[N:9]1)C1C=CC=CC=1.CS(C)=O.CC([O-])(C)C.[K+].[NH4+].[Cl-]>C1COCC1>[CH2:31]([N:18]1[C:19](=[O:30])[C:20]2[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:13]([C:11]3[CH:12]=[N:8][NH:9][CH:10]=3)=[N:14][C:15]=2[N:16]=[C:17]1[N:34]1[CH2:35][CH2:36][CH2:37][CH2:38]1)[CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 671351238-(1-Benzyl-1H-pyrazol-4-yl)-1-propyl-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one

Product 1

HCID 671351511-Propyl-8-(1H-pyrazol-4-yl)-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-oneYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 8-(1-Benzyl-1H-pyrazol-4-yl)-1-propyl-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.154 g, 0.29 mmol), and DMSO (0.2 ml, 2.9 mmol) was taken in THF (10 ml). 0.5M solution of KOtBu (4 ml, 2.0 mmol) in THF was added at 0° C. and stirred for 18 hours. After adding saturated NH4Cl solution, the compound was extracted with ethyl acetate (2×10 ml). Organic layer was washed with brine (2×10 ml), dried over Na2SO4. Solvent was evaporated and purified by preparative TLC to get pure 1-Propyl-8-(1H-pyrazol-4-yl)-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one as white solid (89 mg, 70%)

Workup

  1. extractionthe compound was extracted with ethyl acetate (2×10 ml)
  2. washOrganic layer was washed with brine (2×10 ml)
  3. dry with materialdried over Na2SO4
  4. customSolvent was evaporated
  5. custompurified by preparative TLC

Sources & evidence

ORD record
ord-d0ef404f529f4c7293c9b86620160aa4
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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