Benzenesulfonyl chloride → Benzenesulfonic acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl ester

HRID 705580Notes

Reaction equation

HRID 705580 reaction equation
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:12][N:11]([CH:10]=[N:9][C:3]1[C:2]([F:1])=[CH:7][N:6]=[C:5]([O:8][S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])[N:4]=1)[CH3:13]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 178484257HCID 178484257, compound

Product 1

HCID 57818439Benzenesulfonic acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl esterYield 50.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (0.10 g, 0.54 mmol) in pyridine (2 mL) was added benzene sulfonyl chloride (0.106 g, 0.60 mmol) and the mixture was agitated on an orbital shaker for 16 h at room temperature. The reaction mixture was partitioned between EtOAc and saturated aq NaHCO3, and the organic phase was dried over solid MgSO4, filtered, and concentrated under reduced pressure. Purification by reverse phase chromatography (H2O/MeCN gradient) afforded the title compound (0.089 g, 46% yield) as a white solid: mp 124-125° C.; 1H NMR (300 MHz, CDCl3) δ 8.54 (s, 1H), 8.12-8.07 (m, 3H), 7.73-7.66 (m, 1H), 7.62-7.56 (m, 2H), 3.21 (s, 6H); HPLC-MS (ESI) m/z 325 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and saturated aq NaHCO3
  2. dry with materialthe organic phase was dried over solid MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by reverse phase chromatography (H2O/MeCN gradient)

Sources & evidence

ORD record
ord-fd3c3c3207084ea9ab7a33a01b3c4ad1
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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