Ethanol → HCID 14013540, compound

HRID 1904860Notes

Reaction equation

HRID 1904860 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][N:25]2[C:30](=[O:31])[C:29]3[CH:32]=[C:33]([CH3:35])[S:34][C:28]=3[NH:27][C:26]2=S)[CH2:19][CH2:18]1.[OH-].[K+].C([OH:41])C.OO>O>[OH2:1].[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][N:25]2[C:30](=[O:31])[C:29]3[CH:32]=[C:33]([CH3:35])[S:34][C:28]=3[NH:27][C:26]2=[O:41])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 14013522HCID 14013522, compound

Product 1

HCID 14013540HCID 14013540, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 3 parts of 3-[2-[4-[[3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidinyl]ethyl]-2,3-dihydro-6-methyl-2-thioxothieno[2,3-d]pyrimidin-4(1H)-one, 4.3 parts of potassium hydroxide, 56 parts of ethanol and 5.5 parts of water were added dropwise 45 parts of a hydrogen peroxide solution 3%. The whole was stirred overnight. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanone. The product was filtered off and dried, yielding 1.7 parts (58%) of 3-[2-[4-[[3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidinyl]ethyl]-6-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione monohydrate; mp. 135.4° C. (496).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from 2-propanone
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-3205b094ff2044bc87e55d829d44f517
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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