Ammonium Hydroxide → 4-chloro-5-methyl-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one

HRID 2088872Notes

Reaction equation

HRID 2088872 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([CH3:14])[CH2:9][C:10](OC)=[O:11])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[OH-].[NH4+:17]>>[Cl:1][C:2]1[C:7]2[CH:8]([CH3:14])[CH2:9][C:10](=[O:11])[NH:17][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 86666567HCID 86666567, compound

Product 1

HCID 866665664-chloro-5-methyl-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-oneYield 60%

Conditions

Temperature
60 °C

Procedure

Add methyl 3-(4,6-dichloropyrimidin-5-yl)butanoate (24.00 g, 96.35 mmol) to 30% aqueous ammonium hydroxide (100.00 mL, 7.5 eq) in a sealed tube. Seal and stir the mixture at 60° C. overnight. Cool the mixture in an ice bath. Filter the solid and wash with cold water to give 4-chloro-5-methyl-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one (11.35 g, 60%). MS (ES) m/z=198 [M]+.

Workup

  1. customSeal
  2. temperatureCool the mixture in an ice bath
  3. filtrationFilter the solid
  4. washwash with cold water

Sources & evidence

ORD record
ord-e03e0e76bbdc45a68b1f5c345ae2dcda
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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