Sodium Chloride → HCID 60123473, compound

HRID 2416432Notes

Reaction equation

HRID 2416432 reaction equation
C([O:4][C@H:5]([CH3:25])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:17]([CH3:22])=[CH:18][C:19]([CH3:21])=[N:20][C:13]=2[N:12]([CH3:23])[C:11]1=[O:24])(=O)C.[OH-].[K+].[Cl-].[Na+]>CO.O>[OH:4][C@H:5]([CH3:25])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:17]([CH3:22])=[CH:18][C:19]([CH3:21])=[N:20][C:13]=2[N:12]([CH3:23])[C:11]1=[O:24]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 69732524HCID 69732524, compound

Product 1

HCID 60123473HCID 60123473, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of the crude (R)-3-(5-acetoxyhexyl)-1,5,7-trimethylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione in methanol (10 ml) and was added a solution of potassium hydroxide (200 mg) in water (1 ml) was added. After stirring at room temperature for 3 hours, saturated aqueous sodium chloride solution (5 ml) and water (5 ml) were added. The methanol was evaporated under reduced pressure and the aqueous mixture was extracted with ethyl acetate (20 ml). The organic layer was applied to a short column of silica gel. Elution with ethyl acetate afforded (R)-3-(5-hydroxyhexyl)-1,5,7-trimethylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (227 mg, 84% yield) as an oil. 1H NMR (300 MHz, CDCl3) δ 1.19 (d, 3H), 1.33-1.79 (m, 6H), 2.53 (s, 3H), 2.77 (s, 3H), 3.68 (s, 3H), 3.80 (m, 1H), 4.04 (t, 2H), 6.82 (s, 1H).

Workup

  1. additionwas added
  2. customThe methanol was evaporated under reduced pressure
  3. extractionthe aqueous mixture was extracted with ethyl acetate (20 ml)
  4. washElution with ethyl acetate

Sources & evidence

ORD record
ord-daeb438a288e42ffa9aab136d3f8d8f4
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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