Diethyl Ether → HCID 18456518, compound

HRID 1863923Notes

Reaction equation

HRID 1863923 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([Cl:18])=[N:13][C:12]([C:19]([F:22])([F:21])[F:20])=[N:11][C:10]=2[CH2:9]1)C1C=CC=CC=1.CCOCC>C(OCC)(=O)C.CO>[ClH:18].[F:22][C:19]([F:20])([F:21])[C:12]1[N:13]=[CH:14][C:15]2[CH2:16][CH2:17][NH:8][CH2:9][C:10]=2[N:11]=1

Participants

5

Reactant 2

HCID 3283Diethyl Ether2×HCID 184565217-Benzyl-4-chloro-2-(trifluoromethyl)-5,6,7,8-tetrahydropyrido[3,4-D]pyrimidine

Product 1

HCID 18456518HCID 18456518, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A flask containing a solution of 23.4 g (71.41 mmol) of 7-benzyl-4-chloro-2-(trifluoromethyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine in 285 mL of ethyl acetate and 530 mL of methanol was purged with nitrogen, and 2 g of 10% Pd/C was added. The mixture was stirred under 1 atm of hydrogen until the reaction was judged complete by TLC analysis (about 7.5 h total). The mixture was filtered through Celite, and the Celite washed with methanol. The organics were concentrated in vacuo and the resultant pale yellow oil was triturated with 400 mL of ether. Crystals formed and an additional 400 mL of ether was added. The mixture was stirred overnight. The resultant solid was collected by filtration and dried in vacuo to give off-white crystals that contained an impurity by TLC analysis. The crystals were dissolved in a minimum amount of methanol. Ether was added to turbidity and the mixture was warmed on a steam bath. Crystals formed and the mixture was allowed to cool to ambient temperature and aged for 30 min. It was then filtered. The collected solid was dried in vacuo to give the title compound as a white crystalline solid. LC-MS 204 (M+1).

Workup

  1. customwas purged with nitrogen, and 2 g of 10% Pd/C
  2. additionwas added
  3. customwas judged complete by TLC analysis (about 7.5 h total)
  4. filtrationThe mixture was filtered through Celite
  5. washthe Celite washed with methanol
  6. concentrationThe organics were concentrated in vacuo
  7. customthe resultant pale yellow oil was triturated with 400 mL of ether
  8. customCrystals formed
  9. stirringThe mixture was stirred overnight
  10. filtrationThe resultant solid was collected by filtration
  11. customdried in vacuo
  12. customto give off-white crystals that
  13. temperaturethe mixture was warmed on a steam bath
  14. customCrystals formed
  15. filtrationIt was then filtered
  16. customThe collected solid was dried in vacuo

Sources & evidence

ORD record
ord-8b0b9371ee2e4470970923f80a910288
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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