HCID 69732890, compound → 476623-49-1

HRID 2416429Notes

Reaction equation

HRID 2416429 reaction equation
C([N:8]1[C:13]2[N:14]([CH3:29])[C:15](=[O:28])[N:16]([CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([N:25]([CH3:27])[CH3:26])[CH3:24])[C:17](=[O:18])[C:12]=2[C:11](=[O:30])[CH:10]=[C:9]1[CH3:31])C1C=CC=CC=1.[H][H]>[Pd].C(O)(=O)C>[CH3:29][N:14]1[C:13]2[NH:8][C:9]([CH3:31])=[CH:10][C:11](=[O:30])[C:12]=2[C:17](=[O:18])[N:16]([CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([N:25]([CH3:27])[CH3:26])[CH3:24])[C:15]1=[O:28]

Participants

5

Reactant 2

HCID 69732890HCID 69732890, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 60123477476623-49-1Yield 117.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of (R)-8-benzyl-1,7-dimethyl-3-(5-(N,N-dimethylamino)hexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (80 mg), acetic acid (10 ml) and 10% Pd/C (20 mg) was treated with hydrogen gas (50 psi) on a Parr shaker for 18 hours. The mixture was filtered through a pad of celite and the solids were rinsed with acetic acid. The combined filtrates were concentrated under reduced pressure and then coevaporated with toluene (2×50 ml) to remove remaining acetic acid to provide (R)-1,7-dimethyl-3-(5-(N,N-dimethylamino)hexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (74 mg, 99% yield) as a beige powder. 1H NMR (300 MHz, CDCl3) δ 1.15 (d, 3H), 1.20-1.50 (m, 3H), 1.52-2.00 (m, 3H), 1.97 (s, 3H), 2.40 (s, 3H), 2.55(s, 6H), 3.15 (m, 1H), 3.58 (s, 3H), 3.97 (t, 2H), 6.40 (s, 1H), 9.50 (broad s, 1H).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washthe solids were rinsed with acetic acid
  3. concentrationThe combined filtrates were concentrated under reduced pressure
  4. customto remove

Sources & evidence

ORD record
ord-2f2698cccd264f679a242b1513b6cc72
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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