Hydrochloric Acid → HCID 54300677, compound

HRID 431687Notes

Reaction equation

HRID 431687 reaction equation
C([O:6][C@@H:7]([C:9]1[N:14]=[C:13]([Cl:15])[CH:12]=[CH:11][N:10]=1)[CH3:8])(=O)CCC.Cl>O1CCOCC1>[Cl:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([C@H:7]([OH:6])[CH3:8])[N:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10944226(R)-1-(4-chloro-pyrimidin-2-yl)ethyl butyrate

Product 1

HCID 54300677HCID 54300677, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-1-(4-chloro-pyrimidin-2-yl)-ethyl butyrate (prepared according to the method of Preparation Seven, 250 mg, 1.1 mmol) in dioxane (0.9 mL) was added concentrated hydrochloric acid (0.9 mL). This mixture was allowed to stir at room temperature for 5 h, quenched with saturated aqueous sodium bicarbonate followed by solid sodium bicarbonate until no more gas evolution was evident. Dichloromethane was added and the layers were separated. The aqueous phase was extracted with dichloromethane (3×) and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated to give 125 mg (71%) of the title compound as a pale yellow oil. 1H NMR (CDCl3, 400 MHz) δ 8.59 (d, 1H), 7.25 (d, 1H), 4.92 (q, 1H), 3.81 (br s, 1H), 1.56 (d, 3H); MS (APCI) 159, 161 (MH+).

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. additionDichloromethane was added
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with dichloromethane (3×)
  5. dry with materialthe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-1c007d4778dc4b7b97c4f4281aa6c3f1
Source dataset
uspto-grants-2003_12
Patent number
US06660740B1

Reaction notes

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