Water → HCID 57587932, compound

HRID 1782149Notes

Reaction equation

HRID 1782149 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16]S[C:11]=2[N:10]=[C:9]1[CH:19]([NH:23]CCC1OCCO1)[CH:20]([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-]=[N+:32]=[N-:33].[Na+].[OH2:35]>CN(C=O)C>[N:23]([CH:19]([C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16][O:35][C:11]=2[N:10]=1)[CH:20]([CH3:22])[CH3:21])=[N+:32]=[N-:33]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 68828677HCID 68828677, compound

Product 1

HCID 57587932HCID 57587932, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 5-benzyl-6-(1-bromo-2-methyl-propyl)-3-methyl-5H-isoxazolo[5,4-d]pyramidin-4-one (method 44) (100 mg, 0.266 mmol) and sodium azide (34.5 mg, 0.53 mmol) in DMF (2 ml) was stirred at 60° C. for 1 h. Water (5 ml) was added to the mixture and then extracted with EtOAc (3×20 ml). The combined organic phases were washed with brine (10 ml), dried, concentrated to obtain 6-(1-azido-2-methyl-propyl)-5-benzyl-3-methyl-5H-isoxazolo[5,4-d]pyrimidin-4-one which was purified by ISCO (Hexane-EtOAc). 50 mg (56%) of a colorless oil was obtained. m/z: 339 (MH+), 1H NMR (DMSO-d6): 0.60 (d, 3H), 0.95 (d, 3H), 2.25 (m, 1H), 2.45 (s, 3H), 4.19 (d, 1H), 5.30 (d, 1H), 5.42 (d, 1H), 7.12-7.30 (m, 5H).

Workup

  1. extractionextracted with EtOAc (3×20 ml)
  2. washThe combined organic phases were washed with brine (10 ml)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8f8306cfc3fd4915a6ed4a52ebd8f881
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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