3-tert-Butylaniline → HCID 136041735, compound

HRID 880072Notes

Reaction equation

HRID 880072 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].[N:12]1([C:18]2[N:19]=[C:20]([CH2:25][C:26]([O-])=[O:27])[NH:21][C:22](=[O:24])[CH:23]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[Na+].O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO>[CH3:3][C:1]([C:5]1[CH:6]=[C:7]([NH:8][C:26](=[O:27])[CH2:25][C:20]2[NH:21][C:22](=[O:24])[CH:23]=[C:18]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:19]=2)[CH:9]=[CH:10][CH:11]=1)([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 793343-tert-ButylanilineHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136041735HCID 136041735, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

224 mg of 3-(tert-butyl)aniline are added to a solution of 261 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 2 of Example 1 in 10 ml of methanol. The reaction mixture is stirred at ambient temperature for 5 minutes and then 442 mg of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride hydrate are added. The resulting mixture is thus stirred for 30 minutes at ambient temperature. The reaction mixture is concentrated under reduced pressure. The evaporation residue is taken up with 10 ml of water and 10 ml of ethyl acetate. The resulting product is then stirred for 30 minutes. The precipitate formed is filtered off. 235 mg of N-[3-(2-methylpropan-2-yl)phenyl]-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are thus obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. stirringThe resulting mixture is thus stirred for 30 minutes at ambient temperature
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. stirringThe resulting product is then stirred for 30 minutes
  4. customThe precipitate formed
  5. filtrationis filtered off

Sources & evidence

ORD record
ord-84820cd287714b61b94bfba9f5f7efe4
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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