Methanol → N-[3-methoxycarbonylphenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine

HRID 2161Notes

Reaction equation

HRID 2161 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH3:33]O>>[CH3:33][O:2][C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 19689579N-[3-carboxy-phenyl]-4-(2-(3-hydroxy-propyl-amino)-4-pyridyl)-2-pyrimidineamine

Product 1

HCID 19689556N-[3-methoxycarbonylphenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine

Procedure

2.0 g (5.4 mmol) of N-[3-carboxy-phenyl]-4-(2-(3-hydroxy-propyl-amino)-4-pyridyl)-2-pyrimidineamine and 0.28 ml (5.4 mmol) of conc. sulfuric acid are boiled under RF in 150 ml of methanol for 24 h. After cooling to RT, the reaction mixture is concentrated to half the volume, diluted with 100 ml of ethyl acetate and extracted twice with 50 ml of buffer (pH 7) each time. The organic phase is dried (Na2SO4) and concentrated. Crystallisation (methylene chloride/methanol) gives N-[3-methoxycarbonylphenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine; m.p. 162°-163°, FAB-MS: 380 (M+ +H).

Workup

  1. concentrationthe reaction mixture is concentrated to half the volume
  2. additiondiluted with 100 ml of ethyl acetate
  3. extractionextracted twice with 50 ml of buffer (pH 7) each time
  4. dry with materialThe organic phase is dried (Na2SO4)
  5. concentrationconcentrated
  6. customCrystallisation (methylene chloride/methanol)

Sources & evidence

ORD record
ord-4d75cb7565874f338140d42a8ca396c2
Source dataset
uspto-grants-1998_03
Patent number
US05728708

Reaction notes

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