Thionyl Chloride → 3-(Chloromethyl)-6-methyl-2-phenylpyrazolo[1,5-a]pyrimidine

HRID 1924286Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]=2[CH2:11]O)[CH:7]=1.S(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[Cl:21][CH2:11][C:10]1[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][N:6]2[CH:7]=[C:2]([CH3:1])[CH:3]=[N:4][C:5]=12

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methanol x143 (2.4 mmol, 1 eq, 0.58 g) in toluene (20 ml) is added thionyl chloride (4.8 mmol, 2 eq, 353 μ□l). The mixture is heated at 80° C. for 2 hours. The resulting mixture is cooled down to room temperature and the solvent removed under reduced pressure to afford 3-(chloromethyl)-6-methyl-2-phenylpyrazolo[1,5-a]pyrimidine x146, to which 5 ml of dry DMF are added.

Workup

temperatureThe resulting mixture is cooled down to room temperature
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-14706bbf83cc43abac36937523bf07f1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178533B2

Reaction notes

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