Hydrochloric Acid → HCID 10400931, compound

HRID 859975Notes

Reaction equation

HRID 859975 reaction equation
C([O:3][CH:4](OCC)[C:5]1[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=2)=[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][N:7]2[N:6]=1)C.Cl>O1CCCC1>[CH3:21][S:20][C:16]1[N:15]=[C:14]([C:13]2[C:5]([CH:4]=[O:3])=[N:6][N:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=23)[CH:19]=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10043128HCID 10043128, compound

Product 1

HCID 10400931HCID 10400931, compoundYield 790%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(diethoxymethyl)-3-[2-(methylthio)pyrimidin-4-yl]pyrazolo[1,5-a]pyridine (1.3 g, 3.8 mmol) in tetrahydrofuran (20 mL) was treated with aqueous hydrochloric acid (10 mL 4 M), the resultant solution was stirred for 18 h. The solvents were removed in vacuo and the residue was taken up in dichloromethane and the pH adjusted to >7 with 1N aqueous sodium hydroxide. The organic layer was washed with brine. The aqueous layer was extracted with dichloromethane and the combined organics were dried over sodium sulfate. Filtration and concentration followed flash chromatography on silica gel (1:1 to 1:2 hexane-ethyl acetate) provided 3-[2-(Methylthio)pyrimidin-4-yl]pyrazolo[1,5-a]pyridine-2-carbaldehyde (804 mg, 790%) as a yellow solid. 1H NMR (CDCl3) δ 10.42 (s, 1H), 8.61–8.58 (m, 3H), 7.92 (d, 1H), 7.44 (m, 1H), 7.12 (m, 1H), 2.65 (s, 3H); MS m/z 271 (M+1).

Workup

  1. customThe solvents were removed in vacuo
  2. washThe organic layer was washed with brine
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-72e087f30bcb49789c23b6df9aade226
Source dataset
uspto-grants-2006_12
Patent number
US07153863B2

Reaction notes

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