Benzenesulfonyl chloride → Benzenesulfonic Acid 4-amino-5-fluoropyrimidin-2-yl Ester

HRID 1500027Notes

Reaction equation

HRID 1500027 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([OH:9])[N:3]=1.[C:10]1([S:16](Cl)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>N1C=CC=CC=1>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([O:9][S:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:18])=[O:17])[N:3]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 178509007HCID 178509007, compound

Product 1

HCID 57818591Benzenesulfonic Acid 4-amino-5-fluoropyrimidin-2-yl EsterYield 29%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 4-amino-5-fluoro-pyrimidin-2-ol (0.177 g, 1.4 mmol) in pyridine (5 mL) was added benzene sulfonyl chloride (0.284 g, 1.6 mmol) and the mixture was stirred at room temperature for 2 h. The reaction mixture was evaporated to dryness and the crude material purified by reverse phase chromatography to yield the title compound (0.106 g, 29% yield) as a white solid: mp 145-146° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.05-8.00 (m, 3H), 7.9-7.75 (m, 3H), 7.70-7.63 (m, 2H); HPLC-MS (ESI) m/z 270 (M+H)+, 268 (M−H)−.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe crude material purified by reverse phase chromatography

Sources & evidence

ORD record
ord-16d14c7bfe2e471f90036a0c19202914
Source dataset
uspto-grants-2015_12
Patent number
US09204653B2

Reaction notes

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