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

HRID 1073102Notes

Reaction equation

HRID 1073102 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-Bromo-4-chloro-7-(2-hydroxyethoxymethyl)pyrrolo-[2,3-d]pyrimidine (8b, 0.7 g) 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 gel column (20×3 cm) with 5% MeOH in CHCl3 yielded a solid after evaporation of the appropriate UV absorbing fractions.

Workup

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

Sources & evidence

ORD record
ord-7249ee2c000541fdaa951c9b39dbd2b5
Source dataset
uspto-grants-1990_11
Patent number
US04968686

Reaction notes

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