Methanol → HCID 178418674, compound

HRID 6528

Reaction equation

HRID 6528 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]#[C:10][N:11]1[C:16]([OH:17])=[C:15]2[CH:18]=[C:19]([NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[N:20]=[C:14]2[N:13]=[CH:12]1.CO.N1C2C(=CC=CC=2)C=CC=1.[H][H]>[Pd].CCOCC.C(Cl)(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH:9]=[CH:10][N:11]1[C:16]([OH:17])=[C:15]2[CH:18]=[C:19]([NH:21][C:22](=[O:27])[C:23]([CH3:25])([CH3:24])[CH3:26])[N:20]=[C:14]2[N:13]=[CH:12]1

Participants

8

Reactant 4

HCID 887MethanolHCID 7047QuinolineHCID 178418361HCID 178418361, compoundHCID 178418609HCID 178418609, compound

Product 1

HCID 178418674HCID 178418674, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 2 g of 3-(3-tetrahydropyr-2-yloxyprop-1-yn-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine, 40 ml of methanol, 20 ml of chloroform, 40 mg of 5% palladium on barium sulfate, and 40 mg of synthetic quinoline is stirred under 1 atmosphere hydrogen pressure for 40 min. The solvent then is removed by evaporation and the residue diluted with methylene chloride. The methylene chloride solution is filtered through silica gel with 2% methanol in methylene chloride to remove catalyst and the filtrate then concentrated to give an oil which upon adding ether yields 3-(3-tetrahydropyr-2-yloxyprop-1-en-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine which can be further purified through column chromatography eluting with ethyl acetate and recrystallization using ethyl acetate.

Workup

  1. customThe solvent then is removed by evaporation
  2. additionthe residue diluted with methylene chloride
  3. filtrationThe methylene chloride solution is filtered through silica gel with 2% methanol in methylene chloride
  4. customto remove catalyst
  5. concentrationthe filtrate then concentrated
  6. customto give an oil which

Sources & evidence

ORD record
ord-68835ea9559e4264a057fa5856eb6da6
Source dataset
uspto-grants-1993_09
Patent number
US05248775

Linked notes

Loading…