Ammonium formate → (tetrahydro-pyran-4-yl)-[(S)-3-(5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidin-1-yl]-methanone

HRID 242332Notes

Reaction equation

HRID 242332 reaction equation
C([N:8]1[CH2:31][CH2:30][C:11]2[N:12]=[CH:13][N:14]=[C:15]([O:16][C@H:17]3[CH2:21][CH2:20][N:19]([C:22]([CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[O:23])[CH2:18]3)[C:10]=2[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[O:27]1[CH2:28][CH2:29][CH:24]([C:22]([N:19]2[CH2:20][CH2:21][C@H:17]([O:16][C:15]3[C:10]4[CH2:9][NH:8][CH2:31][CH2:30][C:11]=4[N:12]=[CH:13][N:14]=3)[CH2:18]2)=[O:23])[CH2:25][CH2:26]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57495346[(S)-3-(6-benzyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidin-1-yl]-(tetrahydro-pyran-4-yl)-methanone

Product 1

HCID 57495345(tetrahydro-pyran-4-yl)-[(S)-3-(5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidin-1-yl]-methanoneYield 98.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of [(S)-3-(6-benzyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidin-1-yl]-(tetrahydro-pyran-4-yl)-methanone (10.9 g, 25.8 mmol) was dissolved in methanol (300 mL) and Pd(OH)2 on Carbon (2 g, 14.24 mmol) and ammonium formate (3.35 g, 51.6 mmol) were added. The reaction mixture was refluxed for 2 h. The reaction was cooled down to rt, the reaction mixture was filtered and evaporated under high vacuum for 2 h to yield (tetrahydro-pyran-4-yl)-[(S)-3-(5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidin-1-yl]-methanone (8.45 g, 95% yield) as a light yellow foam. 1H NMR (400 MHz, DMSO-d6, 298K) δ ppm 1.44-1.67 (m, 4H) 2.08-2.32 (m, 2H) 2.55-2.83 (m, 3H) 2.96 (t, 2H) 3.22-3.96 (m, 11H) 5.53-5.68 (m, 1H) 8.49-8.59 (m, 1H). LCMS: [M+H]+=333.5, Rt(6)=1.24 min.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. filtrationthe reaction mixture was filtered
  3. customevaporated under high vacuum for 2 h

Sources & evidence

ORD record
ord-51940db5ea02499e89beda7431e65578
Source dataset
uspto-grants-2014_02
Patent number
US08653092B2

Reaction notes

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