Ammonia → HCID 22821688, compound

HRID 223167Notes

Reaction equation

HRID 223167 reaction equation
[CH2:1]([O:4][C:5]1[C:6]2[CH:17]=[CH:16][N:15]([C@@H:18]3[O:38][C@H:37]([CH2:39][O:40][CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[C@@H:28]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@@H:19]3[O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:7]=2[N:8]=[C:9](S(C)(=O)=O)[N:10]=1)[CH:2]=[CH2:3].[NH3:48]>>[NH2:48][C:9]1[N:10]=[C:5]([O:4][CH2:1][CH:2]=[CH2:3])[C:6]2[CH:17]=[CH:16][N:15]([C@@H:18]3[O:38][C@H:37]([CH2:39][O:40][CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[C@@H:28]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@@H:19]3[O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:7]=2[N:8]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 54131015HCID 54131015, compound

Product 1

HCID 22821688HCID 22821688, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 13.5 g of 4-allyloxy-2-methylsulfonyl-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine and 250 ml of liquid ammonia is heated at 100° C. for 2 hours and allowed to evaporate in a stream of nitrogen. The residue is dissolved in ethyl acetate and chromatographed over silica gel with ethyl acetate to provide 9.3 g of pure 2-amino-4-allyloxy-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine.

Workup

  1. customto evaporate in a stream of nitrogen
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. customchromatographed over silica gel with ethyl acetate

Sources & evidence

ORD record
ord-dd90e3f7a27f43d1af8e6efb7ef7c12f
Source dataset
uspto-grants-1982_10
Patent number
US04352795

Reaction notes

Loading…