Trimethylsilyldiazomethane → HCID 86724890, compound

HRID 510455Notes

Reaction equation

HRID 510455 reaction equation
[C:1](O)(=O)C.[CH3:5][C:6]1[C:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[C:9]2[NH:10][C:11]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[CH:12][C:13](=[O:14])[N:8]2[N:7]=1.C[Si](C=[N+]=[N-])(C)C>ClCCl.CO>[CH3:1][N:7]1[N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]3[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=3)[N:10]=[C:9]2[C:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[C:6]1[CH3:5]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 178475838HCID 178475838, compound

Product 1

HCID 86724890HCID 86724890, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 2-methyl-3-(2-methylbenzyl)-5-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one acetate (500 mg, 1.281 mmol) in dichloromethane/methanol (30 mL/15 mL) was added trimethylsilyldiazomethane (1.3 mL, 2.561 mmol). The mixture was stirred at room temperature for 16 h. Then the mixture was concentrated under reduced pressure. The residue was purified by a silica gel chromatography to give the titled compound (223 mg, 51%); LC/MS: MS (ES+) m/e 345 (MH+); 1H NMR (300 MHz, CDCl3) δ ppm 2.27 (s, 3H), 2.42 (s, 3H), 4.04 (s, 2H), 4.24 (s, 3H), 6.51 (s, 1H), 7.10-7.20 (m, 4H), 7.88 (d, J=5.7 Hz, 2H), 8.70 (d, J=5.7 Hz, 2H).

Workup

  1. concentrationThen the mixture was concentrated under reduced pressure
  2. customThe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-909ac79a9fed4c798eeb114c30d492fb
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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