Water → 2-amino-3,5-dihydro-5-benzyl-4H-Pyrrolo[3,2-d]pyrimidin-4-one

HRID 1805858Notes

Reaction equation

HRID 1805858 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:11])[C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].O>C(Cl)Cl.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[NH2:1][C:2]1[NH:3][C:4](=[O:11])[C:5]2[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 1354610039-Deazaguanine

Product 1

HCID 1359874852-amino-3,5-dihydro-5-benzyl-4H-Pyrrolo[3,2-d]pyrimidin-4-oneYield 88%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-amino-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (336.7 mg, 2.0 mmol) in CH2Cl2 (14.3 mL) was added benzyl bromide (0.26 mL, 2.2 mmol) and TBABr (644 mg, 2.0 mmol). The reaction mixture was cooled to 0° C., and to it was added 50% NaOH (1.7 mL). The resulting mixture was stirred for 2 h as it warmed from 0° C. to room temperature. Water was then added, and the solution was washed with CHCl3. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by column chromatography, eluting with CH2Cl2/Acetone (5:1-1:1), afforded the product as a tan solid (423 mg, 82%)

Workup

  1. temperaturewarmed from 0° C. to room temperature
  2. washthe solution was washed with CHCl3
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography
  8. washeluting with CH2Cl2/Acetone (5:1-1:1)

Sources & evidence

ORD record
ord-c99bcda01ff24f4098633bccd96659f2
Source dataset
uspto-grants-2013_01
Patent number
US08354532B2

Reaction notes

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