Benzene → HCID 23349876, compound

HRID 2058166Notes

Reaction equation

HRID 2058166 reaction equation
C([Li])CCC.[CH:6]([N:9]([CH:28]([CH3:30])[CH3:29])[CH2:10][CH2:11][NH:12][C:13]1[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:14]=1)([CH3:8])[CH3:7].C1C=CC=CC=1.[CH3:37][N:38]([CH3:42])[C:39](Cl)=[O:40]>O>[CH3:37][N:38]([CH3:42])[C:39]([N:12]([CH2:11][CH2:10][N:9]([CH:6]([CH3:7])[CH3:8])[CH:28]([CH3:30])[CH3:29])[C:13]1[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:14]=1)=[O:40]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6598Dimethylcarbamoyl ChlorideHCID 23349934HCID 23349934, compoundHCID 178418339Butyllithium

Product 1

HCID 23349876HCID 23349876, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, n-butyl lithium solution (22.2 ml, 0.036 mole) is added dropwise with stirring to a solution of 2-(2-diisopropylaminoethylamino)-4-methyl-6-benzyloxypyrimidine (12.4 g, 0.036 mole) in 75 ml. of dry benzene at 25° to 30° C. with occasional cooling over a 20 minute period. After stirring an additional 3/4 hour, dimethylcarbamoyl chloride (4.3 g, 0.04 mole) is added dropwise over 15 minutes. The reaction is stirred at room temperature for 16 hours. After cooling, the reaction mixture is treated with water and the benzene layer is separated. The crude product is extracted into 1 N-hydrochloric acid. This aqueous solution is basified and the product is extracted into ether, dried over sodium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel eluting with 25% methanol, 75% chloroform yields N,N-dimethyl-N'-(2-diisopropylaminoethyl)-N'-(4-methyl-6-benzyloxy-2-pyrimidinyl)urea.

Workup

  1. stirringThe reaction is stirred at room temperature for 16 hours
  2. temperatureAfter cooling
  3. customthe benzene layer is separated
  4. extractionThe crude product is extracted into 1 N-hydrochloric acid
  5. extractionthe product is extracted into ether
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e053c8f58e6a4923ac7b45a15f7499bb
Source dataset
uspto-grants-1980_07
Patent number
US04215121

Reaction notes

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