Allyl bromide → HCID 86667335, compound

HRID 334115Notes

Reaction equation

HRID 334115 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:10]([CH3:11])[C:9](=[O:12])[CH:8]([CH3:13])[C:6]=2[N:7]=1.[CH3:20][Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:30](Br)[CH:31]=C>C1COCC1>[CH2:13]([C:8]1([CH3:20])[C:6]2[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:5]=2[N:10]([CH3:11])[C:9]1=[O:12])[CH:30]=[CH2:31]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 73554663HCID 73554663, compound

Product 1

HCID 86667335HCID 86667335, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To 2-chloro-5,7-dimethyl-4-morpholino-5H-pyrrolo[3,2-d]pyrimidin-6(7H)-one (92.0 mg, 0.32 mmol) in anhydrous THF (5 mL) under N2 at −78° C. was added dropwise 1.0 M lithium hexamethyldisilazide in THF (0.65 mL, 0.65 mmol). The reaction mixture was stirred at −78° C. under N2 for 60 minutes. Allyl bromide (0.062 mL, 0.72 mmol) dissolved in 0.5 mL of THF was added, and the reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was quenched with saturated aqueous NH4Cl solution and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography eluted with 10 to 100% ethyl acetate/heptane gave 84.3 mg (80.3%) of 7-allyl-2-chloro-5,7-dimethyl-4-morpholino-5H-pyrrolo[3,2-d]pyrimidin-6(7H)-one. MS(ESI) m/z: 323.1 [M+1]+.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at ambient temperature for 16 h
  3. customThe reaction mixture was quenched with saturated aqueous NH4Cl solution
  4. additiondiluted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel chromatography
  10. washeluted with 10 to 100% ethyl acetate/heptane

Sources & evidence

ORD record
ord-6587a531eba5466d85e3c8383b035f1b
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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