Hydrochloric Acid → HCID 60123474, compound

HRID 2416424Notes

Reaction equation

HRID 2416424 reaction equation
Cl.C([O:5][C@H:6]([CH3:33])[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:16](=[O:17])[C:15]2[C:18](=[O:30])[CH:19]=[C:20]([CH3:29])[N:21]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]=2[N:13]([CH3:31])[C:12]1=[O:32])(=O)C>CO>[CH2:22]([N:21]1[C:14]2[N:13]([CH3:31])[C:12](=[O:32])[N:11]([CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([OH:5])[CH3:33])[C:16](=[O:17])[C:15]=2[C:18](=[O:30])[CH:19]=[C:20]1[CH3:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69733083HCID 69733083, compound

Product 1

HCID 60123474HCID 60123474, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

37% Aqueous hydrochloric acid (5 ml) was added to a solution of the crude (R)-3-(5-acetoxyhexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione in methanol (20 ml). After stirring at room temperature for 18 hours, the solution was concentrated under reduced pressure. The residue was treated with water (20 ml) and extracted with ethyl acetate (2×20 ml). The combined extracts were concentrated under reduced pressure to provide an oil which solidified on standing. The solid was recrystallized (ethyl acetate-hexanes) to afford (R)-8-Benzyl-1,7-dimethyl-3-(5-hydroxyhexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.26 g, 60% yield for 2 steps) as a white powder. 1H NMR (300 MHz, CDCl3) δ 1.19 (d, 3H), 1.35-1.52 (m, 4H), 1.54-1.70 (m, 2H), 2.47 (s,3H), 3.63 (s, 3H), 3.78 (m, 1H), 4.05 (t, 2H), 5.29 (s, 2H), 6.54 (s, 1H), 7.25-7.55 (m, 5H).

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. additionThe residue was treated with water (20 ml)
  3. extractionextracted with ethyl acetate (2×20 ml)
  4. concentrationThe combined extracts were concentrated under reduced pressure
  5. customto provide an oil which
  6. customThe solid was recrystallized (ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-4e475390b6f54f08b80c3f2ce666bfdb
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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