4,6-Dichloropyrimidine → HCID 53257457, compound

HRID 576671Notes

Reaction equation

HRID 576671 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[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:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 12822521HCID 12822521, compound

Product 1

HCID 53257457HCID 53257457, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5.309 g N-(4-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. 3.813 g N-[4-(6-Chloro-pyrimidin-4-ylamino)-benzyl]-methanesulfonamide was obtained above 98% purity in 46% overall yield. For analitical results and compound identification see Table 1. The compound was used as a starting material in the preparation of Example 34-58 and 76.

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-899f91952af24317a00453864991e95a
Source dataset
uspto-grants-2015_05
Patent number
US09040529B2

Reaction notes

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