Tetrahydrofuran → ((2R,3S,4R,5R)-5-{4-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-3,4-dihydroxytetrahydrofuran-2-yl)methyl sulfamate

HRID 552695Notes

Reaction equation

HRID 552695 reaction equation
C([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2C=N[C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][C@@H:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21]2)[O:7][C@@H:6]1[CH2:29][O:30][S:31]([NH2:34])(=[O:33])=[O:32])(=O)C.O1CC[CH2:37][CH2:36]1.N.C[OH:42]>>[S:31](=[O:33])(=[O:32])([O:30][CH2:29][C@@H:6]1[C@@H:5]([OH:4])[C@@H:9]([OH:42])[C@H:8]([N:10]2[C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH:19][C@@H:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH2:22][CH2:21]4)[C:16]=3[CH:37]=[CH:36]2)[O:7]1)[NH2:34]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21705897Ammonia methanolHCID 86607295HCID 86607295, compound

Product 1

HCID 86607296((2R,3S,4R,5R)-5-{4-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-3,4-dihydroxytetrahydrofuran-2-yl)methyl sulfamateYield 66%

Procedure

(2R,3S,5R)-2-{[(Aminosulfonyl)oxy]methyl}-5-{6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-9H-purin-9-yl}tetrahydrofuran-3-yl acetate (96 mg, 0.20 mmol) was dissolved in 2.6 mL of 7M NH3/MeOH and stirred for one hour. Approximately 1 mL tetrahydrofuran was added, and the resulting solution was stirred for 3 hours. The solvent was removed in vacuo and the residue purified by silica gel chromatography (0% to 10% MeOH/CH2Cl2) to afford 59 mg (66%) of the title compound.

Workup

  1. stirringthe resulting solution was stirred for 3 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by silica gel chromatography (0% to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-953f456f716848d980c02dccd62dc47d
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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