Sodium Hydroxide → 2-Butyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine

HRID 1487242Notes

Reaction equation

HRID 1487242 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([C:10]1[NH:11][C:12](=O)[C:13]2[NH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)[CH2:7][CH2:8][CH3:9].[OH-].[Na+]>>[CH2:6]([C:10]1[N:11]=[C:12]([Cl:3])[C:13]2[NH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 1370052332-Butyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

Product 1

HCID 1183828482-Butyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidineYield 91.2%

Procedure

Phosphorus oxychloride (20 mL, 21.46 mmol) was added to 2-butyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (1.69 g). The resultant mixture was heated at 100° C. After 4 hours the reaction mixture was cooled to room temperature then poured onto ice. The aqueous phase was treated with aqueous sodium hydroxide solution (5M) until the pH was 7. The resultant mixture was extracted with ethyl acetate (2×150 mL). The combined organic phase were washed with brine, dried (Na2SO4), filtered and evaporated to give the title compound (1.69 g)

Workup

  1. additionthen poured onto ice
  2. extractionThe resultant mixture was extracted with ethyl acetate (2×150 mL)
  3. washThe combined organic phase were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ae5c141428364f578ce378acafbd3d39
Source dataset
uspto-grants-2016_08
Patent number
US09428512B2

Reaction notes

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