Hydrochloric Acid → HCID 60123475, compound

HRID 2416434Notes

Reaction equation

HRID 2416434 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](=[O:21])[NH:20][C:13]=2[N:12]([CH3:23])[C:11]1=[O:24])(=O)C.Cl.C(=O)(O)[O-].[Na+]>CO>[CH3:23][N:12]1[C:13]2[NH:20][C:19](=[O:21])[CH:18]=[C:17]([CH3:22])[C:14]=2[C:15](=[O:16])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([OH:4])[CH3:25])[C:11]1=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 69733504HCID 69733504, compound

Product 1

HCID 60123475HCID 60123475, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (R)-3-(5-acetoxyhexyl)-1,5-dimethylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione (175 mg, 0.50 mmol), methanol (5 ml) and 12 M aqueous hydrochloric acid (1 ml) was stirred at room temperature for 18 hours and then treated with saturated aqueous sodium bicarbonate solution (10 ml). After concentrating under reduced pressure to remove the methanol, the aqueous mixture was extracted with ethyl acetate (20 ml). The extract was applied to a short column of silica gel and eluted with ethyl acetate to afford (R)-1,5-dimethyl-3-(5-hydroxyhexyl)pyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione (50 mg, 32% yield) as a white powder. 1H NMR (300 MHz, CDCl3) δ 1.17 (d, 3H), 1.30-1.71 (m, 6H), 2.67 (s, 3H), 3.57 (s, 3H), 3.72-3.88 (m, 1H), 3.98 (t, 2H), 6.23 (s, 1H).

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customto remove the methanol
  3. extractionthe aqueous mixture was extracted with ethyl acetate (20 ml)
  4. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-3e1fad57478a46d2bd02be0d225dd865
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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