Potassium hydroxy sulfite → 2-Chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carboxylic acid

HRID 2091855Notes

Reaction equation

HRID 2091855 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]([CH:12]=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.[OH:20]OS([O-])=O.[K+]>CN(C=O)C>[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]([C:12]([OH:20])=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 534880072-Chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 584050092-Chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carbaldehyde (0.56 g) was reacted with Oxone (1.1 eq) in DMF (10 mL) overnight. The DMF was removed under vacuum and the reaction mixture was brought up into water. The pH was adjusted to 2-3 and product crashed out of solution. The solid was collected by filtration and dried to afford 0.45 g of 2-chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carboxylic acid as a light yellow solid.

Workup

  1. customThe DMF was removed under vacuum
  2. filtrationThe solid was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-5a72efc090d24985ac4ede933259db6e
Source dataset
uspto-grants-2013_05
Patent number
US08440651B2

Reaction notes

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