Triethylamine → 2-{[2-(Methanesulfonylamino)ethyl]amino}-4-(3-methylanilino)pyrimidine-5-carboxamide

HRID 2303309Notes

Reaction equation

HRID 2303309 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[NH2:13][CH2:14][CH2:15][NH:16][C:17]1[N:22]=[C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=2)[C:20]([C:31]([NH2:33])=[O:32])=[CH:19][N:18]=1>C(OCC)(=O)C>[CH3:1][S:2]([NH:13][CH2:14][CH2:15][NH:16][C:17]1[N:22]=[C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=2)[C:20]([C:31]([NH2:33])=[O:32])=[CH:19][N:18]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 98173492-(2-Aminoethylamino)-4-(m-tolylamino)pyrimidine-5-carboxamide

Product 1

HCID 184608482-{[2-(Methanesulfonylamino)ethyl]amino}-4-(3-methylanilino)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 114 μl portion of methanesulfonyl chloride and 205 μl of triethylamine were added to a mixture of 382 mg of 2-(2-aminoethylamino)-4-(3-methylanilino)pyrimidine-5-carboxamide with 10 ml of ethyl acetate, followed by stirring at room temperature for 3.5 hours. The reaction mixture was washed with water and saturated brine, and then the organic layer was dried over anhydrous magnesium sulfate. This was concentrated under a reduced pressure and the resulting residue was recrystallized from a mixed solvent of methanol and ethyl acetate to obtain 210 mg of 2-{[2-(methanesulfonylamino)ethyl]amino}-4-(3-methylanilino)pyrimidine-5-carboxamide (colorless crystals).

Workup

  1. washThe reaction mixture was washed with water and saturated brine
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationThis was concentrated under a reduced pressure
  4. customthe resulting residue was recrystallized from a mixed solvent of methanol and ethyl acetate

Sources & evidence

ORD record
ord-c1d78e4fc76549d98b5f58066eee71dc
Source dataset
uspto-grants-2002_08
Patent number
US06432963B1

Reaction notes

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