Hydrochloric Acid → Benzenesulfonic Acid 4-amino-5-fluoropyrimidin-2-yl Ester

HRID 705581ノート

反応式

HRID 705581 の反応式
Cl.CN(C=[N:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[C:9]([O:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[N:8]=1)C>>[NH2:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[C:9]([O:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[N:8]=1

参加物

3

反応物 2

HCID 313Hydrochloric AcidHCID 57818439Benzenesulfonic acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl ester

生成物 1

HCID 57818591Benzenesulfonic Acid 4-amino-5-fluoropyrimidin-2-yl Ester収率 79%

実験手順

To a solution of HCl in doxane (3 mL of 10%) was added benzenesulfonic acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl ester (0.090, 0.3 mmol) and the mixture was agitated on an orbital shaker at room temperature for 1.5 h. The solvent was removed by evaporation and the residue was dissolved in a 1:1 solution of dioxane and water (2.5 mL) and treated with saturated aq NaHCO3 (0.5 mL). After 16 h, the reaction mixture was partitioned between EtOAc and water and the organic phase was dried over Na2SO4, filtered, and the solvent evaporated to yield the title compound (0.059 g, 79% yield) as a white solid: mp 139-141° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.05-8.00 (m, 3H), 7.90-7.75 (m, 3H), 7.70-7.63 (m, 2H); HPLC-MS (ESI) m/z 268 (M−H)−, 270 (M+H)+.

後処理

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in a 1:1 solution of dioxane and water (2.5 mL)
  3. additiontreated with saturated aq NaHCO3 (0.5 mL)
  4. waitAfter 16 h
  5. customthe reaction mixture was partitioned between EtOAc and water
  6. dry with materialthe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent evaporated

出典と根拠

ORDレコード
ord-b96aadf04cd74525a79d008038b9e395
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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