Sodium hydride → 5-((Benzyloxy)methyl)-2-butyl-4-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine

HRID 1487244Notes

Reaction equation

HRID 1487244 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]2[NH:16][CH:15]=[C:14]([I:17])[C:6]=2[N:7]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[N:9]=1.Cl[CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([O:20][CH2:19][N:16]1[C:5]2[C:4]([Cl:3])=[N:9][C:8]([CH2:10][CH2:11][CH2:12][CH3:13])=[N:7][C:6]=2[C:14]([I:17])=[CH:15]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 1183828472-Butyl-4-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 1183828495-((Benzyloxy)methyl)-2-butyl-4-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidineYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.338 g, 60% in oil, 14.08 mmol) was added portionwise to a stirred solution of 4-chloro-7-iodo-2-butyl-5H-pyrrolo[3,2-d]pyrimidine (2.19 g, 6.53 mmol) in DMF (30 mL) cooled in an ice-bath. After 30 minutes benzyl chloromethyl ether (1.13 mL, 1.278 g, 8.16 mmol) was added and the reaction stirred at room temperature. The reaction mixture was quenched with water and the resultant mixture partitioned between ethyl acetate (150 mL) and water (150 mL). The organic phase was washed with water then saturated aqueous sodium chloride solution, dried (Na2SO4), filtered and evaporated. The sample was dissolved in dichloromethane and purified by chromatography on silica (100 g) using a gradient of 0-100% ethyl acetate-cyclohexane over 30 minutes. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a yellow oil (2.82 g).

Workup

  1. temperaturecooled in an ice-bath
  2. customThe reaction mixture was quenched with water
  3. customthe resultant mixture partitioned between ethyl acetate (150 mL) and water (150 mL)
  4. washThe organic phase was washed with water
  5. dry with materialsaturated aqueous sodium chloride solution, dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe sample was dissolved in dichloromethane
  9. custompurified by chromatography on silica (100 g)
  10. customover 30 minutes
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-59b2e4c04cb94addab235cd02180bd47
Source dataset
uspto-grants-2016_08
Patent number
US09428512B2

Reaction notes

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