Water → HCID 57988795, compound

HRID 889017Notes

Reaction equation

HRID 889017 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[C:12][CH2:13][N:14]2[CH:18]=[C:17]([C:19]3[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:26]4[C:25](=[O:36])[N:24]([CH2:37][CH2:38][CH3:39])[C:23](=[O:40])[N:22]([CH2:41][CH2:42][CH3:43])[C:21]=4[N:20]=3)[CH:16]=[N:15]2)[CH:6]=1)C.[BH4-].[Na+].O>C1COCC1>[OH:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]#[C:12][CH2:13][N:14]2[CH:18]=[C:17]([C:19]3[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:33])([CH3:35])[CH3:34])[C:26]4[C:25](=[O:36])[N:24]([CH2:37][CH2:38][CH3:39])[C:23](=[O:40])[N:22]([CH2:41][CH2:42][CH3:43])[C:21]=4[N:20]=3)[CH:16]=[N:15]2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57988773HCID 57988773, compound

Product 1

HCID 57988795HCID 57988795, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-{4-[2,6-dioxo-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]-pyrazol-1-yl}-prop-1-ynyl)-benzoic acid ethyl ester (50 mg, 0.08 mmol) in THF (5 ml), NaBH4 (5 mg, 0.16 mmol) was added slowly at 0° C. It was stirred for 3 h at room temperature. Water was added to reaction mixture and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and then filtered and concentrated under vacuum. The residue obtained was purified by column chromatography to obtain 8-{1-[3-(3-hydroxymethyl-phenyl)-prop-2-ynyl]-1H-pyrazol-4-yl}-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (25 mg, 54%) as an yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-069030e7c04b420d934fa7fdd355b3f2
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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