Ammonium Chloride → 2-Chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carboxamide

HRID 1043615Notes

Reaction equation

HRID 1043615 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[N:11]=[C:10]([C:12](O)=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.[Cl-].[NH4+].C[N:24](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[N:11]=[C:10]([C:12]([NH2:24])=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584050092-Chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carboxylic acid

Product 1

HCID 584050312-Chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carboxylic acid from Example 118 (0.12 g) was reacted with ammonium chloride (7 eq), HATU (1.5 eq) and DIPEA (4 eq) in DMF (5.2 mL) for 30 minutes. The reaction mixture was then diluted with water and the orange solid was collected by filtration to give 90 mg of 2-chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carboxamide.

Workup

  1. filtrationthe orange solid was collected by filtration

Sources & evidence

ORD record
ord-e5c214ab3fff4b8ca17d5e24c8ce133b
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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