Chloroform → 6-(3,4-Dimethoxyphenyl)-4-(4-mesylaminophenylamino)-2-methylpyrimidine

HRID 4342Notes

Reaction equation

HRID 4342 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)[N:12]=[C:11]([CH3:25])[N:10]=2)=[CH:4][CH:3]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(N(CC)CC)C.C(Cl)(Cl)Cl>ClCCCl>[CH3:24][O:23][C:17]1[CH:16]=[C:15]([C:13]2[N:12]=[C:11]([CH3:25])[N:10]=[C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:3][CH:4]=3)[CH:14]=2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 201522544-(4-Aminophenylamino)-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine

Product 1

HCID 201522626-(3,4-Dimethoxyphenyl)-4-(4-mesylaminophenylamino)-2-methylpyrimidine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-(4-aminophenylamino)-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (1.0 g) in 1,2-dichloroethane (20 ml) were added methanesulfonyl chloride (0.28 ml) and triethylamine (0.83 ml) and the mixture was refluxed for 3 hours. After cooled, chloroform (50 ml) was added thereto, and washed with water. The solution was dried over magnesium sulfate, evaporated, and chromatographed on silica gel eluting with chloroform to give 6-(3,4-dimethoxyphenyl)-4-(4-mesylaminophenylamino)-2-methylpyrimidine (0.45 g).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperatureAfter cooled
  3. washwashed with water
  4. dry with materialThe solution was dried over magnesium sulfate
  5. customevaporated
  6. customchromatographed on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-917a2479c3f9457d87255a214f0059bb
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Reaction notes

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