4-Methyloxybenzyl chloride → 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

HRID 2042079Notes

Reaction equation

HRID 2042079 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[CH:6]=[CH:5][N:4]=1.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>ClCCl.O>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:12]2[CH:13]=[C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=3)[CH:10]=[N:11]2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 497575772-(methylthio)-4-(1H-pyrazol-4-yl)pyrimidine

Product 1

HCID 672523404-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(methylthio)-4-(1H-pyrazol-4-yl)pyrimidine (200 mg, 1 mmol) in dichloromethane (3 mL) and H2O (1 mL) was added 4-methoxybenzylchloride (200 mg, 1.28 mmol) at 0° C. The mixture was stirred at RT overnight. The organic layer was separated, washed with brine and concentrated in vacuo to give crude 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine. 1H NMR (300 MHz, DMSO-d6) δ 8.58 (s, 1H), 8.50, (d, J=5.4 Hz, 1H), 8.16 (s, 1H), 7.40 (d, J=5.4 Hz, 1H), 7.27 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 5.30 (s, 2H), 3.72 (s, 3H), 2.51 (s, 3H); MS (ESI) m/z: 313 (M+H+).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-062efb26340940ecb3bcda93e355b735
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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