Benzoyl chloride → Benzoic Acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl Ester

HRID 705579ノート

反応式

HRID 705579 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](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:4]=1)[CH3:13]

参加物

4

反応物 2

HCID 7412Benzoyl chlorideHCID 178484257HCID 178484257、化合物

生成物 1

HCID 57818967Benzoic Acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl Ester収率 94.4%

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 benzoyl chloride (0.084 g, 0.60 mmol), and the mixture was agitated on an orbital shaker for 16 h at RT. The reaction mixture was partitioned between EtOAc and saturated aq NaHCO3, and the organic phase was dried over solid MgSO4, filtered, and evaporated to give the title compound (0.147 g 94%) as a white solid: mp 136-138° C.; 1H NMR (300 MHz, CDCl3) δ 8.69 (s, 1H), 8.27 (d, J=2.4 Hz, 2H), 8.25-8.20 (m, 2H), 7.69-7.63 (m, 1H), 7.56-7.49 (m, 2H), 3.23 (s, 3H), 3.20 (s, 3H); HPLC-MS (ESI) m/z 289 (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. customevaporated

出典と根拠

ORDレコード
ord-bb488616f0434be7846fc97f08924851
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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