Ammonia → 4-Amino-5-bromo-7-(2-hydroxyethoxymethyl)pyrrolo(2,3-d)pyrimidine

HRID 442563Notes

Reaction equation

HRID 442563 reaction equation
Cl[C:2]1[C:3]2[C:10]([Br:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][OH:16])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:17]>CO>[NH2:17][C:2]1[C:3]2[C:10]([Br:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][OH:16])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 3010392HCID 3010392, compound

Product 1

HCID 1226824-Amino-5-bromo-7-(2-hydroxyethoxymethyl)pyrrolo(2,3-d)pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
125 °C

Procedure

5-Bromo4chloro-7(2-hydroxyethoxymethyl)pyrrolo[2,3-d]pyrimidine (8b, 0.75) was dissolved in dry methanol (10 mL) and methanol saturated with ammonia (40 mL) was then added to this solution. The reaction mixture was heated at 125° C. in a sealed reaction vessel for 10 hours The solvent was removed at 40° C. under reduced pressure and the resulting solid was then subjected to column chromatography. Elution of the silica get column (20×3 cm) with 5% MeOH in CHCl3 yielded a solid after evaporation of the appropriate UV absorbing fractions.

Workup

  1. customwas removed at 40° C. under reduced pressure
  2. washElution of the silica
  3. customget column (20×3 cm) with 5% MeOH in CHCl3
  4. customyielded a solid
  5. customafter evaporation of the appropriate UV
  6. customabsorbing fractions

Sources & evidence

ORD record
ord-53a7ca5051fc4227b5b234ff9f43c0e3
Source dataset
uspto-grants-1999_04
Patent number
USRE036187

Reaction notes

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