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

HRID 705582Notes

Reaction equation

HRID 705582 reaction equation
[F:1][C:2]1[C:3]([NH2:9])=[N:4][C:5](=[O:8])[NH:6][CH:7]=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>[NH2:9][C:3]1[C:2]([F:1])=[CH:7][N:6]=[C:5]([O:8][S:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:18])=[O:17])[N:4]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 178509021HCID 178509021, 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 5-fluorocytosine (0.177 g, 1.4 mmol) in pyridine (5 mL) was added and 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. additionwas added
  2. customThe reaction mixture was evaporated to dryness
  3. customthe crude material purified by reverse phase chromatography

Sources & evidence

ORD record
ord-39606d4d888245beb72c481c7031f0c1
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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