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

HRID 705581노트

반응식

HRID 705581 반응식
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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-b96aadf04cd74525a79d008038b9e395
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174970B2

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