Calciumoxide → HCID 19785288, compound

HRID 256658Notes

Reaction equation

HRID 256658 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[C:5]([CH2:11][CH:12]1[CH2:17][CH2:16][N:15](CC3C=CC=CC=3)[CH2:14][CH2:13]1)=[N:6]2.[O-2].[Ca+2].[H][H]>[Pd].CO>[F:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:4]2[C:3]3[C:7](=[N:8][CH:9]=[N:10][CH:2]=3)[N:6]=[C:5]2[CH2:11][CH:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 6850728CalciumoxideHCID 19785240HCID 19785240, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19785288HCID 19785288, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 15 parts of 6-chloro-7-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]-methyl]-7H-purine. 5 parts of calcium oxide and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in water. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia. (95:5→85:15 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 5.8 parts (54%) of 7-[(4-fluorophenyl)methyl]-8-(4-piperidinylmethyl)-7H-purine as a residue (compound 55).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. extractionThe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated

Sources & evidence

ORD record
ord-8e5d7db6240d4f9b87316412817c1ec6
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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