Methylamine → 4-[3'-(3-Methylamino-2-hydroxypropoxy)anilino]6-(3'-methylanilino) pyrimidine

HRID 1418005Notes

Reaction equation

HRID 1418005 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][NH2:28]>C(O)C.O>[CH3:27][NH:28][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

5

Reactant 2

HCID 6329MethylamineHCID 867538554-[3'-(2,3-Epoxypropoxy)anilino]6-(3'-methylanilino) pyrimidine

Product 1

HCID 701870144-[3'-(3-Methylamino-2-hydroxypropoxy)anilino]6-(3'-methylanilino) pyrimidineYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

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 and 33% methylamine in ethanol and NHP was stirred over 2 days at room 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-methylamino-2-hydroxypropoxy)anilino]6-(3'-methylanilino) pyrimidine is 46% yield, m.p. 88°-90° 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-7907808590f3499f9926e9f19ec97b8c
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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