Ethyl chloroformate → HCID 19785250, compound

HRID 256655Notes

Reaction equation

HRID 256655 reaction equation
[Cl:1][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.[C:33](Cl)(=[O:37])[O:34][CH2:35][CH3:36].[OH-].[NH4+]>CC1C=CC=CC=1>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=1)[C:5]([CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([C:33]([O:34][CH2:35][CH3:36])=[O:37])[CH2:16][CH2:17]1)=[N:6]2

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 19785240HCID 19785240, compound

Product 1

HCID 19785250HCID 19785250, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 16 parts of 6-chloro-7-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-7H-purine, 4.65 parts of ethyl carbonochloridate and 180 parts of methylbenzene was stirred for 2 hours at reflux temperature. After cooling, the reaction mixture was treated with ammonium hydroxide and the product was extracted with methylbenzene. The extract was washed with water, dried, filtered and evaporated, yielding 18.7 parts (100%) of ethyl 4-[[6-chloro-7-[(4-fluorophenyl)methyl]-7H-purin-8-yl]methyl]-1-piperidinecarboxylate as a residue (compound 28).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. extractionthe product was extracted with methylbenzene
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-92aac68774bc42a18da1c236c5a74cd6
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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