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

HRID 705581Notes

Reaction equation

HRID 705581 reaction equation
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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-b96aadf04cd74525a79d008038b9e395
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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