4-(6-((2H-pyran-4(3H,5H,6H)-ylidene)methyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine → 4-(2-chloro-6-((tetrahydro-2H-pyran-4-yl)methyl)pyrido[3,2-d]pyrimidin-4-yl)morpholine

HRID 1043640Notes

Reaction equation

HRID 1043640 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[CH:7][C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[C:13]([Cl:24])[N:14]=[C:15]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:16]=3[N:17]=2)[CH2:3][CH2:2]1>C(O)C>[Cl:24][C:13]1[N:14]=[C:15]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[C:16]2[N:17]=[C:8]([CH2:7][CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:9]=[CH:10][C:11]=2[N:12]=1

Participants

3

Reactant 1

HCID 584050234-(6-((2H-pyran-4(3H,5H,6H)-ylidene)methyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 584049764-(2-chloro-6-((tetrahydro-2H-pyran-4-yl)methyl)pyrido[3,2-d]pyrimidin-4-yl)morpholineYield 49.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(6-((2H-Pyran-4(3H,5H,6H)-ylidene)methyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine (0.22 g) was brought up in ethanol (30 mL) and ethyl acetate (30 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 for 2.5 hours. The reaction was filtered thru celite and purified by flash column chromatography to obtain 0.11 g 4-(2-chloro-6-((tetrahydro-2H-pyran-4-yl)methyl)pyrido[3,2-d]pyrimidin-4-yl)morpholine.

Workup

  1. customethyl acetate (30 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-7731bd3b58744c159fd18d041202bfd4
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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