Water → DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(cyclopropylmethoxy)benzyl]aminopyrimidine

HRID 703862Notes

Reaction equation

HRID 703862 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[Cl:25][C:26]1[N:31]=[C:30]([NH:32][CH:33]([CH2:41][CH3:42])[C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1.[CH:45]1([CH2:48]Cl)[CH2:47][CH2:46]1.O.C1(C)C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[Cl:25][C:26]1[N:31]=[C:30]([NH:32][CH:33]([CH2:41][CH3:42])[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:48][CH:45]3[CH2:47][CH2:46]3)=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 80013(Chloromethyl)cyclopropaneHCID 131716268DL-5 Chloro-6-ethyl-4-(alphaethyl-4-hydroxybenzylamino)pyrimidine

Product 1

HCID 131716269DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(cyclopropylmethoxy)benzyl]aminopyrimidineYield 41.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.1 g of dl-5-chloro-6-ethyl-4-(α-ethyl-4-hydroxybenzyl)aminopyrimidine dissolved in 30 ml of N,N-dimethylformamide was added 0.4 g of cyclopropylmethyl chloride, and the mixture was stirred at 90° to 100° C. for 8 hours. After completion of the reaction, the reaction mixture was charged into water and the separated oily product was extracted with ethyl acetate. The extract was washed with water, dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The oily product obtained was isolated by column chromatography (Wako Gel C-200, trade name, eluted with toluene:ethyl acetate=7:1) to give 0.5 g of the desired product as pale yellow liquid.

Workup

  1. customAfter completion of the reaction
  2. extractionthe separated oily product was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe oily product obtained

Sources & evidence

ORD record
ord-57af93b0144a47169f51c294ab26eb2b
Source dataset
uspto-grants-1991_01
Patent number
US04985426

Reaction notes

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