3,5-Dimethylaniline → HCID 9967835, compound

HRID 2214785Notes

Reaction equation

HRID 2214785 reaction equation
CS([C:4]1[N:9]=[C:8]([C:10]2[NH:14][N:13]=[CH:12][C:11]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][N:5]=1)=O.CS(C1N=C(C2NN=CC=2C2C=CC=CC=2)C=CN=1)(=O)=O.[CH3:42][C:43]1[CH:44]=[C:45]([CH:47]=[C:48]([CH3:50])[CH:49]=1)[NH2:46]>>[CH3:42][C:43]1[CH:44]=[C:45]([NH:46][C:4]2[N:9]=[C:8]([C:10]3[NH:14][N:13]=[CH:12][C:11]=3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:7]=[CH:6][N:5]=2)[CH:47]=[C:48]([CH3:50])[CH:49]=1

Participants

4

Reactant 3

HCID 79493,5-DimethylanilineHCID 21948461HCID 21948461, compoundHCID 21948509HCID 21948509, compound

Product 1

HCID 9967835HCID 9967835, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(methylsulfinyl)-4-(4-phenyl-1H-pyrazol-5-yl)pyrimidine and 2-(methylsulfonyl)-4-(4-phenyl-1H-pyrazol-5-yl)pyrimidine (3-4, 3-5, 186 mg, 0.62 mg,) and 3,5-dimethylaniline (2 mL, excess) was heated at 90° C. for 24 hours. The reaction mixture was purified by flash chromatography. Elution with CH2Cl2 to 30% EtOAc/CH2Cl2 gave N-(3,5-dimethylphenyl)-4-(4-phenyl-1H-pyrazol-5-yl)pyrimidin-2-amine (3-6) as a pale yellow solid. 1H NMR (500 MHz, CDCl3) δ 8.26 (d, 1H, J=5 Hz), 7.66 (s, 1H), 7.38–7.44 (m, 5 H), 7.21 (br s, 2H), 7.04 (br s, 1H), 6.75 (br s, 1H), 6.71 (d, 1H, J=5 Hz), 2.34 (s, 6H).

Workup

  1. customThe reaction mixture was purified by flash chromatography
  2. washElution with CH2Cl2 to 30% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-6a915eb5a7154dba8f5859c00ff7cf16
Source dataset
uspto-grants-2006_09
Patent number
US07109204B2

Reaction notes

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