Methanol → 4-amino-1-((2R,3S,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-3-hydroxy-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

HRID 2205187Notes

Reaction equation

HRID 2205187 reaction equation
C([O:4][C@H:5]1[C@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@:8]([CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH:18]([F:20])[F:19])[O:7][C@H:6]1[N:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[N:32][C:31]1=[O:37])(=O)C.CO>N>[NH2:36][C:33]1[CH:34]=[CH:35][N:30]([C@H:6]2[C@@H:5]([OH:4])[C@H:9]([O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@:8]([CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([CH:18]([F:19])[F:20])[O:7]2)[C:31](=[O:37])[N:32]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 118294215(2R,3S,4S,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-tetrahydrofuran-3-yl acetate

Product 1

HCID 1182943934-amino-1-((2R,3S,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-3-hydroxy-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of compound 36 (0.112 g, 0.21 mmol) in NH3.MeOH (4 mL) was stirred at 60° C. for 12 h and then cooled and evaporated to dryness under reduced pressure to give 37 as a white solid. LC-MS: (M+H)+=474.2

Workup

  1. temperaturecooled
  2. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6b1e484cf78042cbb58fb751791b8056
Source dataset
uspto-grants-2016_06
Patent number
US09370569B2

Reaction notes

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