2-(2-Methylpropyl)oxirane → HCID 22139594, compound

HRID 1826529Notes

Reaction equation

HRID 1826529 reaction equation
[N+:1]([C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][NH:14][C:7]2=[N:6][C:5]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)([O-:3])=[O:2].[CH2:21]([CH:25]1[CH2:27][O:26]1)[CH:22]([CH3:24])[CH3:23].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>CN(C=O)C>[OH:26][CH:25]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:27][N:14]1[C:7]2=[N:6][C:5]([C:15]3[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=3)=[C:4]([N+:1]([O-:3])=[O:2])[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 909902-(2-Methylpropyl)oxiraneHCID 2733832Lithium HexamethyldisilazideHCID 135830902HCID 135830902, compound

Product 1

HCID 22139594HCID 22139594, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In a 100 mL RBF with stirrer bar was charged 3-nitro-2-pyridin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (1.0 g) and 2-isobutyl-oxirane (0.7 g) in DMF (7 mL) under nitrogen. A solution of LiHMDS (1N in THF, 7 mL) was added to the mixture, resulting a red solution. Affter being heated at 80° C. overnight the mixture was cooled to room temperature and was partitioned between CH2Cl2 and NH4Cl (aq.). The organic phase was further washed with H2O, dried with Na2SO4, concentrated, and eluted on silica gel (0–7% 2N NH3-MeOH in DCM) to afford the product that was used directly in the next step. M+1 374.

Workup

  1. customresulting a red solution
  2. temperaturewas cooled to room temperature
  3. customwas partitioned between CH2Cl2 and NH4Cl (aq.)
  4. washThe organic phase was further washed with H2O
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. washeluted on silica gel (0–7% 2N NH3-MeOH in DCM)
  8. customto afford the product that

Sources & evidence

ORD record
ord-6ee9866635f94d1c8a021d7874a680c2
Source dataset
uspto-grants-2006_05
Patent number
US07049318B2

Reaction notes

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