Water → HCID 68283893, compound

HRID 1527254Notes

Reaction equation

HRID 1527254 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:12]2[CH:11]=[N:10][CH:9]=[N:8][C:7]=2[NH:6][CH:5]=1.Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].O>CN(C=O)C>[C:18]([O:17][C:15](=[O:16])[CH2:14][N:6]1[C:7]2[N:8]=[CH:9][N:10]=[CH:11][C:12]=2[C:4]([Br:3])=[CH:5]1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 107980055-bromo-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 68283893HCID 68283893, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To suspension of NaH (60% in mineral oil, 34 mg, 0.85 mmol) in DMF (1.5 mL) at 0° C. under nitrogen atmosphere was added a solution of 5-bromo-7H-pyrrolo[2,3-d]pyrimidine (140 mg, 0.71 mmol) in DMF (1.5 mL). The reaction mixture was stirred at 0° C. for 30 min and tert-butyl bromoacetate (104 μL, 0.71 mmol) was slowly added. The mixture was further stirred at RT for 30 min, then poured into water and extracted with EtOAc (×3). The combined organic extracts were washed with water, dried (Na2SO4), filtered and concentrated. MS (UPLC/MS): 312.3/314.2 [M+H]+.

Workup

  1. stirringThe mixture was further stirred at RT for 30 min
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-53c356b00fa349bca46e003b01f05c76
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…