Water → HCID 69733509, compound

HRID 2416428Notes

Reaction equation

HRID 2416428 reaction equation
[N:1]([C@H:4]([CH3:31])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[C:13]2[C:16](=[O:28])[CH:17]=[C:18]([CH3:27])[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]=2[N:11]([CH3:29])[C:10]1=[O:30])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][C@H:4]([CH3:31])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[C:13]2[C:16](=[O:28])[CH:17]=[C:18]([CH3:27])[N:19]([CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:12]=2[N:11]([CH3:29])[C:10]1=[O:30]

Participants

5

Reactant 3

HCID 962WaterHCID 11776Triphenylphosphine2×HCID 86591000HCID 86591000, compound

Product 1

HCID 69733509HCID 69733509, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (R)-3-(5-azidohexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (380 mg, 0.90 mmol), triphenylphosphine (260 mg, 0.99 mmol), water (0.1 ml) and tetrahydrofuran (15 ml) was stirred at room temperature for 18 hours followed by heating at 500 C for 4 hours. Another portion of triphenylphosphine (100 mg) was added and the mixture was heated at 65° C. for 18 hours. After concentration under reduced pressure, the residue was treated with 1.0 M aqueous hydrochloric acid (10 ml) and ethyl acetate (10 ml), followed by extraction of the organic layer with 1.0 M aqueous hydrochloric acid (2×10 ml). The combined aqueous layers were made slightly basic (pH˜8) by addition of aqueous potassium hydroxide solution and extracted with ethyl acetate (2×20 ml). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to afford (R)-3-(5-aminohexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (155 mg, 43% yield) as a beige powder. 1H NMR (300 MHz, CDCl3) δ 1.05 (d, 3H), 1.39 (broad s, 4H), 1.66 (m, 2H), 1.90 (broad s, 1H), 2.45 (s, 3H), 2.81 (broad s, 1H), 3.61 (s, 3H), 4.00 (t, 2H), 5.25 (s, 2H), 6.51 (s, 1H), 7.25-7.55 (m, 5H).

Workup

  1. temperatureby heating at 500 C for 4 hours
  2. temperaturethe mixture was heated at 65° C. for 18 hours
  3. concentrationAfter concentration under reduced pressure
  4. additionthe residue was treated with 1.0 M aqueous hydrochloric acid (10 ml) and ethyl acetate (10 ml)
  5. extractionfollowed by extraction of the organic layer with 1.0 M aqueous hydrochloric acid (2×10 ml)
  6. additionby addition of aqueous potassium hydroxide solution
  7. extractionextracted with ethyl acetate (2×20 ml)
  8. dry with materialThe combined organic extracts were dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d345402a6f34425eab050c7470c8199f
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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