4,6-Dichloropyrimidine → N-({3-[(6-chloropyrimidin-4-yl)amino]phenyl}methyl)methanesulfonamide

HRID 576669Notes

Reaction equation

HRID 576669 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][NH:6][S:7]([CH3:10])(=[O:9])=[O:8].[Cl:14][C:15]1[CH:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:14][C:15]1[N:16]=[CH:17][N:18]=[C:19]([NH:1][C:2]2[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=2)[CH2:5][NH:6][S:7]([CH3:10])(=[O:9])=[O:8])[CH:20]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 34174207N-(3-aminobenzyl)methanesulfonamide

Product 1

HCID 53257231N-({3-[(6-chloropyrimidin-4-yl)amino]phenyl}methyl)methanesulfonamideYield 43.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5.309 g N-(3-Amino-benzyl)-methanesulfonamide (obtained in Step 2, 26.5 mmol) and 4.739 g 4,6-dichloropyrimidine (31.81 mmol) was dissolved in 120 cm3 of isopropyl-alcohol, 6.93 cm3 N,N-diisopropyl-ethylamine (5.140 g, 39.76 mmol) was added and the mixture was refluxed for four days. The reaction mixture was cooled to room temperature and the precipitated compound was filtered off. The light yellow product was washed well with diethyl-ether and air-dried. 3.612 g N-[3-(6-Chloro-pyrimidin-4-ylamino)-benzyl]-methanesulfonamide was obtained in more than 98% purity and in 44% overall yield. For analitical results and compound identification see Table 1. The compound was used as a starting material in the preparation of Example 2-32 and 75.

Workup

  1. temperaturethe mixture was refluxed for four days
  2. filtrationthe precipitated compound was filtered off
  3. washThe light yellow product was washed well with diethyl-ether
  4. customair-dried

Sources & evidence

ORD record
ord-d8e4415d5f024744ad28666af3698db6
Source dataset
uspto-grants-2015_05
Patent number
US09040529B2

Reaction notes

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