(2R,3R)-1-Benzyloxy-3-(tert-butyldimethylsiloxy)-2-((2-oxo-4-(1H-1,2,4-triazol-1-yl)pyrimidin-1(2H)-yl)methyl)butane → (2R,3R)-1-Benzyloxy-3-(tert-butyldimethylsiloxy)-2-((4-amino-2-oxo-pyrimidin-1(2H)-yl)methyl)butane

HRID 1754603Notes

Reaction equation

HRID 1754603 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([CH2:21][N:22]1[CH:27]=[CH:26][C:25]([N:28]2C=NC=N2)=[N:24][C:23]1=[O:33])[C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N.CO>[CH2:1]([O:8][CH2:9][C@@H:10]([CH2:21][N:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[N:24][C:23]1=[O:33])[C@H:11]([O:13][Si:14]([C:17]([CH3:19])([CH3:20])[CH3:18])([CH3:15])[CH3:16])[CH3:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 90411164(2R,3R)-1-Benzyloxy-3-(tert-butyldimethylsiloxy)-2-((2-oxo-4-(1H-1,2,4-triazol-1-yl)pyrimidin-1(2H)-yl)methyl)butane

Product 1

HCID 90411042(2R,3R)-1-Benzyloxy-3-(tert-butyldimethylsiloxy)-2-((4-amino-2-oxo-pyrimidin-1(2H)-yl)methyl)butaneYield 95%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

A solution of 18 (1.5 g, 3.2 mmol) in 100 ml of 6 M NH3/MeOH was heated at 100° C. in a Parr bomb for 2 days. The reaction was cooled, concentrated and chromatographed on silica eluting with 10% MeOH in ethyl acetate. Concentration of the product-containing fractions afforded 1.27 g (95%) of 19 as an off-white amorphous solid. 1H NMR (DMSO-d6): δ 7.43 (d, J=7.2 Hz, 1H), 7.29 (m, 5H), 6.97 (br s, 2H), 5.58 (d, J=7.2 Hz), 4.39 (d, J=1.8 Hz, 2H), 3.98 (m, 1H), 3.83 (m, 1H), 3.51 (m, 1H), 3.35 (m, 2H), 2.06 (m, 1H), 1.14 (d, J=6.3 Hz, 3H), 0.85 (s, 9H), 0.02 (s, 3H), 0.00 (s, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customchromatographed on silica eluting with 10% MeOH in ethyl acetate

Sources & evidence

ORD record
ord-bc3b1c4cb2e248a892e2269ef28be56b
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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