Hydrochloric Acid → HCID 69733595, compound

HRID 2416426Notes

Reaction equation

HRID 2416426 reaction equation
C([O:4][C@@H:5]([CH3:32])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:17](=[O:29])[CH:18]=[C:19]([CH3:28])[N:20]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:13]=2[N:12]([CH3:30])[C:11]1=[O:31])(=O)C.Cl.C(=O)(O)[O-].[Na+]>CO>[CH2:21]([N:20]1[C:13]2[N:12]([CH3:30])[C:11](=[O:31])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@@H:5]([OH:4])[CH3:32])[C:15](=[O:16])[C:14]=2[C:17](=[O:29])[CH:18]=[C:19]1[CH3:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 69732875HCID 69732875, compound

Product 1

HCID 69733595HCID 69733595, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)-3-(5-acetoxyhexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.2 g, 2.7 mmol), methanol (10 ml) and 37% aqueous hydrochloric acid (2 ml) was stirred at room temperature for 18 hours. The mixture was treated with saturated aqueous sodium bicarbonate solution (20 ml). The solid was filtered, rinsed with water, and air dried to afford (S)-8-benzyl-1,7-dimethyl-3-(5-hydroxyhexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (850 mg, 89% yield) as a white fluffy powder. 1H NMR (300 MHz, CDCl3) δ 1.17 (d, 3H), 1.38-1.6 (m, 6H), 2.47 (s, 3H), 3.63 (s, 3H), 3.78 (m, 1H), 4.05 (t, 2H), 5.28 (s, 2H), 6.56 (s, 1H), 7.23-7.57 (m, 5H).

Workup

  1. filtrationThe solid was filtered
  2. washrinsed with water, and air
  3. customdried

Sources & evidence

ORD record
ord-bedec1ccbe9d46d1914d787115da6a9f
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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