Sodium Azide → HCID 86591000, compound

HRID 2416427Notes

Reaction equation

HRID 2416427 reaction equation
[CH2:1]([N:8]1[C:13]2[N:14]([CH3:31])[C:15](=[O:30])[N:16]([CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23](OS(C)(=O)=O)[CH3:24])[C:17](=[O:18])[C:12]=2[C:11](=[O:32])[CH:10]=[C:9]1[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:34]=[N+:35]=[N-:36].[Na+]>CS(C)=O>[N:34]([C@H:23]([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19][N:16]1[C:17](=[O:18])[C:12]2[C:11](=[O:32])[CH:10]=[C:9]([CH3:33])[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:13]=2[N:14]([CH3:31])[C:15]1=[O:30])=[N+:35]=[N-:36]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86590999HCID 86590999, compound

Product 1

HCID 86591000HCID 86591000, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of the crude (S)-8-benzyl-1,7-dimethyl-3-(5-methanesulfonyloxyhexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione, dimethylsulfoxide (6 ml) and sodium azide (116 mg, 1.79 mmol) was heated at 600 C for 18 hours. After cooling to room temperature, the mixture was partitioned between water (50 ml) and ethyl acetate (50 ml) and the aqueous layer was extracted with ethyl acetate (50 ml). The combined extracts were rinsed with water and with saturated aqueous sodium chloride solution. Concentrating under reduced pressure afforded (R)-3-(5-azidohexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (380 mg, 99% yield for 2 steps) as an oil. 1H NMR (300 MHz, CDCl3) δ 1.22 (d, 3H), 1.36-1.60)m, 4H), 1.62-1.78 (m, 2H), 2.48 (s, 3H), 3.43 (m, 1H), 3.64 (s, 3H), 4.03 (t, 2H), 5.29 (s, 2H), 6.55 (s, 1H), 7.29

Workup

  1. temperaturewas heated at 600 C for 18 hours
  2. customthe mixture was partitioned between water (50 ml) and ethyl acetate (50 ml)
  3. extractionthe aqueous layer was extracted with ethyl acetate (50 ml)
  4. washThe combined extracts were rinsed with water and with saturated aqueous sodium chloride solution
  5. concentrationConcentrating under reduced pressure

Sources & evidence

ORD record
ord-f00daa1da34948e38de32d5f2058a7b4
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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