Hydrochloric Acid → HCID 60123478, compound

HRID 2416415Notes

Reaction equation

HRID 2416415 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](=[O:22])[CH:18]=[C:19]([CH3:21])[NH:20][C:13]=2[N:12]([CH3:23])[C:11]1=[O:24])(=O)C.Cl.C(=O)(O)[O-].[Na+]>C(OCC)C>[CH3:23][N:12]1[C:13]2[NH:20][C:19]([CH3:21])=[CH:18][C:17](=[O: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 69733596HCID 69733596, compound

Product 1

HCID 60123478HCID 60123478, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of (R)-3-(5-acetoxyhexyl)-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (100 mg, 0.286 mmol), diethyl ether (0.5 ml) and 3 M aqueous hydrochloric acid solution (5 ml) was stirred at room temperature for 18 hours. After treating with saturated aqueous sodium bicarbonate (20 ml), the mixture was extracted with diethyl ether (2×20 ml). The combined extracts were dried over sodium sulfate, and concentrated under vacuum to afford (R)-1,7-dimethyl-3-(5-hydroxyhexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (81 mg, 92% yield) a white powder. 1H NMR (300 MHz, CDCl3) δ 1.17 (d, 3H), 1.30-1.52 (m, 3H), 1.54-1.70 (m, 4H), 2.45 (s, 3H), 3.62 (s, 3H), 3.77 (m, 1H), 4.00 (t, 2H), 6.49 (s, 1H), 12.15 (s, 1H).

Workup

  1. extractionthe mixture was extracted with diethyl ether (2×20 ml)
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dcf351e66c8f4ea199ecade12dfc5ddc
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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