Tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)piperidine-1-carboxylate → Tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidine-1-carboxylate

HRID 2091883Notes

Reaction equation

HRID 2091883 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:5]2[N:11]=[C:10]([CH:12]=[C:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:5]2[N:11]=[C:10]([CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

3

Reactant 1

HCID 58405028Tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)piperidine-1-carboxylate

Product 1

HCID 58404998Tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidine-1-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)piperidine-1-carboxylate (0.72 g) was brought up in ethanol (80 mL) and ethyl acetate (80 mL) and the flask was purged with nitrogen before addition of 10% Palladium on carbon (10 mol %). The reaction was placed under a hydrogen balloon and stirred at room temperature overnight. The reaction was filtered thru celite and purified by flash column chromatography to obtain 0.55 g tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidine-1-carboxylate.

Workup

  1. customethyl acetate (80 mL) and the flask was purged with nitrogen before addition of 10% Palladium on carbon (10 mol %)
  2. filtrationThe reaction was filtered thru celite
  3. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-1c607b30c17446ebad8347cee60cf280
Source dataset
uspto-grants-2013_05
Patent number
US08440651B2

Reaction notes

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