Ammonia → 4-Amino-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c,2-o-dimethyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

HRID 448714Notes

Reaction equation

HRID 448714 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:27][C@H:26]([CH2:28][O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=4[Cl:38])[C@@H:15]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[C@@:12]3([CH3:39])[O:13][CH3:14])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:40]>>[NH2:40][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:27][C@H:26]([CH2:15][O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[C@@H:28]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=4[Cl:38])[C@@:12]3([CH3:39])[O:13][CH3:14])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 235183384-Chloro-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c,2-o-dimethyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 235183374-Amino-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c,2-o-dimethyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

Procedure

To the compound from Step A (735 mg, 1.16 mmol) was added methanolic ammonia (saturated at 0° C.) (20 mL). The mixture was heated in a stainless steel autoclave at 80° C. overnight, then cooled and the content evaporated in vacuo. The crude mixture was purified on silica gel using ethyl acetate/hexane as the eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (504 mg) as colorless foam.

Workup

  1. temperaturecooled
  2. customthe content evaporated 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-833f15e78f0a433d970bb9db5b1fdc46
Source dataset
uspto-grants-2013_07
Patent number
US08481712B2

Reaction notes

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