Ammonia → 4-Amino-7-(2-C-ethyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 2212917Notes

Reaction equation

HRID 2212917 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH2:20][CH3:21])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:22]>CO>[NH2:22][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH2:20][CH3:21])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 865860784-Chloro-7-(2-C-ethyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 99439594-Amino-7-(2-C-ethyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To the compound from Step C (50 mg, 0.16 mmol) was added saturated ammonia in methanol (4 mL). The mixture was stirred at 75° C. for 72 h in a closed container, cooled and evaporated in vacuo. The crude mixture was purified on silica gel using methanol/dichloromethane (1:9) as eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (29 mg) as a colorless powder.

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. customThe crude mixture was purified on silica gel
  4. additionFractions containing the product
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-239b382520304144a0f9431d41059153
Source dataset
uspto-grants-2006_09
Patent number
US07105499B2

Reaction notes

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