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

HRID 2088908Notes

Reaction equation

HRID 2088908 reaction equation
[Cl:1][C:2]1[C:3]2[C@H:11]([CH3:12])[CH2:10][C:9](=[O:13])[N:8](C(OC(C)(C)C)=O)[C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[OH-].[NH4+]>O>[Cl:1][C:2]1[C:3]2[C@H:11]([CH3:12])[CH2:10][C:9](=[O:13])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86666577HCID 86666577, compound

Product 1

HCID 86666575(R)-4-chloro-5-methyl-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-oneYield 87.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
7.5 °C

Procedure

Add (R)-tert-Butyl 4-chloro-5-methyl-7-oxo-6,7-dihydropyrido[2,3-d]pyrimidine-8(5H)-carboxylate (36 g, 1.0 equiv) to water (120 mL) and stir to form a suspension. Add 12N HCl (120 g, 10 equiv) drop wise at 20-30° C. and stir the mixture for 6-8 h. A solution gradually forms. Cool the solution to 5-10° C. and add concentrated ammonium hydroxide (86.4 g, 2.4 equiv) to form a suspension. Stir the suspension for 2-3 h and is filter. Wash the filter cake with cooled water (36 mL), and then slurry with cooled isopropanol (28 g). Filter the slurry and dry the filter cake in vacuo to yield (R)-4-chloro-5-methyl-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one (21 g, 87%). MS (ES) m/z=198 [M]+.

Workup

  1. customto form a suspension
  2. stirringstir the mixture for 6-8 h
  3. customto form a suspension
  4. stirringStir the suspension for 2-3 h
  5. filtrationis filter
  6. washWash the filter cake with cooled water (36 mL)
  7. filtrationFilter the slurry
  8. customdry the filter cake in vacuo

Sources & evidence

ORD record
ord-df02cd7705be4038af0a2a4555c01e78
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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