Water → HCID 57752826, compound

HRID 225997Notes

Reaction equation

HRID 225997 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[N:5]2[N:10]=[CH:11][C:12]([CH:13]=[O:14])=[C:4]2[N:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH2:32](O)[CH2:33][CH2:34][OH:35].O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[N:5]2[N:10]=[CH:11][C:12]([CH:13]3[O:35][CH2:34][CH2:33][CH2:32][O:14]3)=[C:4]2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 104421,3-PropanediolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57752942HCID 57752942, compound

Product 1

HCID 57752826HCID 57752826, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 5,7-dichloro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde (290 mg) in toluene (40 mL) was added pyridinium p-toluenesulfonate (60 mg) and propan-1,3-diol. The mixture was then heated under reflux for 2 h, with azeotropic removal of water. The solution was cooled and evaporated under reduced pressure. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether ⅔ as eluent to give the title compound (310 mg) as a white solid; 1H-NMR (400 MHz, CDCl3) d(ppm): 8.32 (1H, s, 2-H), 5.97 (1H, s, CHO2R), 4.25 (2H, br dd, OCHeq), 4.05 (2H, br t, OCHax), 2.50 (3H, s, 6-Me), 2.25 (1H, m, CCHeqHC), 1.48 (1H, br d, CCHHaxC).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureThe solution was cooled
  3. customevaporated under reduced pressure
  4. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-78d8228622a24d76aa441fa4daba4170
Source dataset
uspto-grants-2009_07
Patent number
US07557110B2

Reaction notes

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