Ammonia → (2R,3R,4R,5R)-2-(4-amino-5-methylpyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol

HRID 2212929Notes

Reaction equation

HRID 2212929 reaction equation
Cl[C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@@:13]3([CH3:21])[OH:14])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:22]>>[NH2:22][C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@@:13]3([CH3:21])[OH:14])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 112207324-Chloro-5-methyl-7-(2-C-methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 3011900(2R,3R,4R,5R)-2-(4-amino-5-methylpyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol

Procedure

To the compound from Step B (0.2 g, 0.64 mmol) was added methanolic ammonia (saturated at 0° C.; 40 mL). The mixture was heated in a stainless steel autoclave at 100° C. for 14 h, then cooled and evaporated in vacuo. The crude mixture was purified on a silica gel column (5×5 cm) with CH2Cl2/MeOH (50/1, 30/1, 20/1) gradient as eluent to give the title compound as a white solid (0.12 g).

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. customThe crude mixture was purified on a silica gel column (5×5 cm) with CH2Cl2/MeOH (50/1, 30/1, 20/1) gradient as eluent

Sources & evidence

ORD record
ord-9f2818aec84a4ae88cd73f72e1638e42
Source dataset
uspto-grants-2006_09
Patent number
US07105499B2

Reaction notes

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