(2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanol → 2-Chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carbaldehyde

HRID 2091854Notes

Reaction equation

HRID 2091854 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[C:5]2[N:11]=[C:10]([CH:12]=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 53488008(2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 534880072-Chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carbaldehydeYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanol 6 (1 g) was reacted with pyridinium chlorochromate (1.1 eq) overnight at room temperature in dichloromethane (25 mL). The reaction was filtered thru celite and run thru a silica plug to get 0.69 g of 2-chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carbaldehyde as a yellow solid after evaporation.

Workup

  1. filtrationThe reaction was filtered thru celite

Sources & evidence

ORD record
ord-b770b990667c4892878f175dcc7f8669
Source dataset
uspto-grants-2013_05
Patent number
US08440651B2

Reaction notes

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