Acetic Acid → Racemic tert-butyl 4-(2-(2,6-dimethylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate

HRID 80787Notes

Reaction equation

HRID 80787 reaction equation
C([N:8]1[CH2:40][CH2:39][C:11]2[N:12]=[C:13]([C:31]3[C:36]([CH3:37])=[CH:35][CH:34]=[CH:33][C:32]=3[CH3:38])[N:14]=[C:15]([N:16]3[C@H:21]([CH3:22])[CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:18]([CH3:30])[CH2:17]3)[C:10]=2[CH2:9]1)C1C=CC=CC=1.C(O)(=O)C>C1COCC1.O.[OH-].[OH-].[Pd+2]>[CH3:38][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]([CH3:37])[C:31]=1[C:13]1[N:14]=[C:15]([N:16]2[C@H:21]([CH3:22])[CH2:20][N:19]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[C@@H:18]([CH3:30])[CH2:17]2)[C:10]2[CH2:9][NH:8][CH2:40][CH2:39][C:11]=2[N:12]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 71244696Racemic tert-Butyl 4-(6-benzyl-2-(2,6-dimethylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate

Product 1

HCID 89685949Racemic tert-butyl 4-(2-(2,6-dimethylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic tert-butyl 4-(6-benzyl-2-(2,6-dimethylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate (0.43 g, 0.794 mmol) in THF (9 mL) and water (3 mL) was added acetic acid (227 μL, 3.97 mmol) and 20% Pd(OH)2 on carbon (50% wet) (0.167 g, 0.238 mmol). The flask was evacuated and purged with hydrogen gas and then placed under a hydrogen atmosphere. After stirring at rt for 1 h the mixture was filtered over Celite®, and the Celite® pad was washed with EtOAc. The filtrate was washed with sat aq NaHCO3 and then the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain racemic tert-butyl 4-(2-(2,6-dimethylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-(trans)-2,5-dimethylpiperazine-1-carboxylate. MS (ESI+) m/z 452.3 (M+H)+.

Workup

  1. customThe flask was evacuated
  2. custompurged with hydrogen gas
  3. filtrationwas filtered over Celite®
  4. washthe Celite® pad was washed with EtOAc
  5. washThe filtrate was washed with sat aq NaHCO3
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91c4c934c8a8455c883fd69ec9ef9326
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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