4-Fluoroaniline → HCID 21349645, compound

HRID 2186665Notes

Reaction equation

HRID 2186665 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@H:15]([OH:16])[C@H:14]([OH:17])[C@@H:13]([CH2:18][O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[O:12]1.[F:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[F:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:2]2[C:3]3[N:4]=[CH:5][N:6]([C:7]=3[N:8]=[CH:9][N:10]=2)[C@@H:11]2[O:12][C@H:13]([CH2:18][O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[C@@H:14]([OH:17])[C@H:15]2[OH:16])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 81531DiisopropylethylamineHCID 56623020HCID 56623020, compound

Product 1

HCID 21349645HCID 21349645, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
22 °C

Procedure

(2R,3R,4S,5R)-2-(6-Chloro-purin-9-yl)-5-(2,2,2-trifluoroethoxymethyl)-tetrahydro-furan-3,4-diol (125 mg) in isopropanol (5 ml) under nitrogen was treated with 4-fluoroaniline (0.08 ml, 90 mg) and diisopropylethylamine (0.28 ml, 210 mg), and the mixture was heated under reflux for 24 h. After cooling to 22° C. the mixture was filtered, the filter cake washed with isopropanol (2 ml) and ether (15 ml) and the solid dried in vacuo to give the title compound as a white solid (70 mg), m.p. 214-5°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 h
  3. filtrationwas filtered
  4. washthe filter cake washed with isopropanol (2 ml) and ether (15 ml)
  5. customthe solid dried in vacuo

Sources & evidence

ORD record
ord-00793caac11e4d76a2bf9918986b51d3
Source dataset
uspto-grants-2002_06
Patent number
US06407076B1

Reaction notes

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