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

HRID 1418003Notes

Reaction equation

HRID 1418003 reaction equation
[O:1]1[CH2:26][CH:2]1[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][CH:25]=1)[NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)[N:12]=[CH:11][N:10]=1.[CH3:27][NH:28][CH3:29]>C(O)C.CN(C=O)C.O>[CH3:27][N:28]([CH3:29])[CH2:26][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][CH:25]=1)[NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 2

HCID 674DimethylamineHCID 867538554-[3'-(2,3-Epoxypropoxy)anilino]6-(3'-methylanilino) pyrimidine

Product 1

HCID 701859524-[3'-(3-Dimethylamino-2-hydroxypropoxy)anilino]6-(3'-methylanilino)pyrimidineYield 55%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Using an analogous reaction procedure to that described in Example 33, a mixture of 4-[3'-(2,3-epoxypropoxy)anilino]6-(3'-methylanilino) pyrimidine, 33% dimethylamine in ethanol and DMF was stirred overnight at ambient temperature. The reaction mixture was diluted with water and extracted with ethyl acetate. The product so obtained was washed with water and with brine, dried (MgSO4) and evaporated. The residue was recrystallised from a mixture of methylene chloride, methanol and hexane to give 4-[3'-(3-dimethylamino-2-hydroxypropoxy)anilino]6-(3'-methylanilino)pyrimidine in 55% yield, m.p. 120°-122° C.;

Workup

  1. customan analogous reaction procedure to
  2. extractionextracted with ethyl acetate
  3. customThe product so obtained
  4. washwas washed with water and with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was recrystallised from a mixture of methylene chloride, methanol and hexane

Sources & evidence

ORD record
ord-ec0594f0a7b744acba96a7c5119e8fe2
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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