Ammonia → HCID 135409288, compound

HRID 223156Notes

Reaction equation

HRID 223156 reaction equation
Cl[C:2]1[C:3]2[CH:14]=[CH:13][N:12]([C@@H:15]3[O:35][C@H:34]([CH2:36][O:37]CC4C=CC=CC=4)[C@@H:25]([O:26]CC4C=CC=CC=4)[C@@H:16]3[O:17]CC3C=CC=CC=3)[C:4]=2[N:5]=[C:6](S(C)(=O)=O)[N:7]=1.C([O:48]CC=C)C=C.[Na].[NH3:53]>>[NH2:53][C:6]1[NH:7][C:2](=[O:48])[C:3]2[CH:14]=[CH:13][N:12]([C@@H:15]3[O:35][C@H:34]([CH2:36][OH:37])[C@@H:25]([OH:26])[C@@H:16]3[OH:17])[C:4]=2[N:5]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 22821689HCID 22821689, compoundHCID 86738583HCID 86738583, compound

Product 1

HCID 135409288HCID 135409288, compound

Procedure

4-Chloro-2-methylsulfonyl-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine reacted sequentially with sodium allyloxide and liquid ammonia and deblocked by hydrogenation in the presence of a catalyst provides 2-amino-7-β-D-arabinofuranosyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidine-4-one. Treatment with phosphoryl chloride and triethyl phosphate provides the corresponding 5'-phosphate compound.

Sources & evidence

ORD record
ord-991607446f164a8a847ee6796d7e0539
Source dataset
uspto-grants-1982_10
Patent number
US04352795

Reaction notes

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