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

HRID 705580ノート

反応式

HRID 705580 の反応式
[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]

参加物

4

反応物 2

HCID 7369Benzenesulfonyl chlorideHCID 178484257HCID 178484257、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-fd3c3c3207084ea9ab7a33a01b3c4ad1
出典データセット
uspto-grants-2015_11
特許番号
US09174970B2

反応ノート

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