3,5-Dimethylaniline → HCID 9879089, compound

HRID 2214789Notes

Reaction equation

HRID 2214789 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][NH:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10](S(C)=O)[N:9]=1)#[N:2].[CH3:17][C:18]1[CH:19]=[C:20]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[NH2:21]>>[C:1]([C:3]1[CH:4]=[N:5][NH:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:21][C:20]2[CH:22]=[C:23]([CH3:25])[CH:24]=[C:18]([CH3:17])[CH:19]=2)[N:9]=1)#[N:2]

Participants

3

Reactant 2

HCID 79493,5-DimethylanilineHCID 21948451HCID 21948451, compound

Product 1

HCID 9879089HCID 9879089, compound

Procedure

A solution of 4-(4-cyano-1H-pyrazol-5-yl)-2-(methylsulfinyl)pyrimidine (4-4, 155 mg, 0.66 mmol) and 3,5-dimethylaniline(3 mL, excess) was heated at 90° C. for 20 hours. The reaction was purified by flash chromatography. Elution with CH2Cl2 to 4% EtOAc/CH2Cl2 gave 4-(4-cyano-1H-pyrazol-5-yl)-2-[(3,5-dimethylphenyl)amino]pyrimidine (4-5) as a solid. 1H NMR (500 MHz, CDCl3) δ 9.00 (s, 1H), 8.63 (dd, 1H, J=5 Hz), 7.50 (dd, 1H, J=5 Hz), 7.31 (br s, 2H), 7.21 (br s, 1H), 6.74 (br s, 1H), 2.35 (s, 6H).

Workup

  1. customThe reaction was purified by flash chromatography
  2. washElution with CH2Cl2 to 4% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-9c11c708b1534a2fb522c4117dfd9a63
Source dataset
uspto-grants-2006_09
Patent number
US07109204B2

Reaction notes

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