Dimethylamine → 4-[4'-(3-Dimethylamino-2-hydroxypropoxy)anilino]6-(3'-methylanilino) pyrimidine

HRID 1417999Notes

Reaction equation

HRID 1417999 reaction equation
[O:1]1[CH2:26][CH:2]1[CH2:3][O:4][C:5]1[CH:25]=[CH:24][C:8]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=3)[N:13]=[CH:12][N:11]=2)=[CH:7][CH:6]=1.[CH3:27][NH:28][CH3:29].O>C(O)C.CN(C=O)C>[CH3:27][N:28]([CH3:29])[CH2:26][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=3)[N:13]=[CH:12][N:11]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 867538534-[4'-(2,3-Epoxypropoxy)anilino]6-(3'-methylanilino) pyrimidine

Product 1

HCID 670151524-[4'-(3-Dimethylamino-2-hydroxypropoxy)anilino]6-(3'-methylanilino) pyrimidineYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[4'-(2,3-epoxypropoxy)anilino]6-(3'-methylanilino) pyrimidine (0.35 g), 33% dimethylamine in ethanol (10 ml) and DMF (5 ml) was stirred at room temperature for 4 hours. The mixture was poured into water, extracted with ethyl acetate and the organic phase evaporated. The residue was recrystallised from a mixture of methylene chloride, methanol and hexane to give 4-[4'-(3-dimethylamino-2-hydroxypropoxy)anilino]6-(3'-methylanilino) pyrimidine in 54% yield, m.p. 192°-195° C.;

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase evaporated
  3. customThe residue was recrystallised from a mixture of methylene chloride, methanol and hexane

Sources & evidence

ORD record
ord-aa3fac6c460e4af0b2f3bccbe790c0b7
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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