N,N-Diethylaniline → HCID 54342542, compound

HRID 1858316Notes

Reaction equation

HRID 1858316 reaction equation
Cl[C:2]1[C:7]([CH2:8][NH:9][C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])=[CH:6][N:5]=[C:4]([S:18][CH3:19])[N:3]=1.[C:20]([O:24][C:25](=[O:38])[NH:26][C:27]([CH3:37])([CH3:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH2:35])[CH:30]=1)([CH3:23])([CH3:22])[CH3:21].C(N(CC)C1C=CC=CC=1)C>ClCCl>[C:20]([O:24][C:25](=[O:38])[NH:26][C:27]([CH3:37])([CH3:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:2]2[C:7]([CH2:8][NH:9][C:10]3[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:17])=[CH:6][N:5]=[C:4]([S:18][CH3:19])[N:3]=2)[CH:30]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 221250524-Chloro-5-(2,6-dichloroanilinomethyl)-2-methylthiopyrimidineHCID 226740811,1-Dimethylethyl N-[2-(3-aminophenyl)-1,1-dimethylethyl]carbamate

Product 1

HCID 54342542HCID 54342542, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 520 mg (1.6 mmol) of 4-chloro-5-(2,6-dichloroanilinomethyl)-2-methylthiopyrimidine, 420 mg (1.6 mmol) of (2-(3-aminophenyl)-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester and 250 mg (1.7 mmol) of N,N-diethylaniline in 5 ml of dichloromethane was heated at 80° C. until the solvent had evaporated and then to 120° C. for 30 minutes and then cooled. The product was purified by flash chromatography on silica gel eluting with diethyl ether/isohexane in a ratio 1:1 to give 350 mg (39%) of (2-(3-[5-[(2,6-dichlorophenylamino)-methyl]-2-methylthiopyrimidin-4-yl-amino]-phenyl)-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester as a white solid. [Mass spectrum (ESI) MH+ =562].

Workup

  1. customhad evaporated
  2. temperaturecooled
  3. customThe product was purified by flash chromatography on silica gel eluting with diethyl ether/isohexane in a ratio 1:1

Sources & evidence

ORD record
ord-896be482f22f46c2ad5d38bf43600a09
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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