Dimethylamine → 2-N-{4-[3-(dimethylamino)-2-hydroxypropoxy]phenyl}-4-N-phenylpyrimidine-2,4-diamine

HRID 347754Notes

Reaction equation

HRID 347754 reaction equation
[NH:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]3[O:25][CH2:24]3)=[CH:17][CH:16]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][NH:27][CH3:28]>CN(C=O)C.CCO>[CH3:26][N:27]([CH2:24][CH:23]([OH:25])[CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:10]2[N:9]=[C:8]([NH:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:13]=[CH:12][N:11]=2)=[CH:20][CH:19]=1)[CH3:28]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 179811334-Anilino-2-(4-(2,3-epoxypropoxy)anilino)pyrimidine

Product 1

HCID 65389852-N-{4-[3-(dimethylamino)-2-hydroxypropoxy]phenyl}-4-N-phenylpyrimidine-2,4-diamineYield 18%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

4-Anilino-2-(4-(2,3-epoxypropoxy)anilino)pyrimidine (Reference Example I-1, 0.61 g, 1.84 mmol) was dissolved in DMF (2 ml) and treated with dimethylamine (6 mmol, 3 ml of a 2M solution in EtOH). After stirring overnight at ambient temperature the reaction mixture was partitioned between EtOAc and water. The organic phase was washed with water, dried over MgSO4 and evaporated at reduced pressure. The residue was purified by chromatography (0.1%NH3 (aq), 3–10% MeOH in DCM as eluent). Upon evaporation of the fractions, an oily product was obtained,this was triturated with ether to give the title product as a white solid (0.126 g, 18%). NMR (300 MHz): 2.2 (s, 6H), 2.3–2.8 (m, 2H), 3.75–3.95 (m, 3H(, 4.82 (brs, 1H), 6.17 (d, 1H), 6.82 (d, 2H), 6.97 (t, 1H), 7.27 (t, 2H), 7.58 (d, 2H), 7.66 (d, 2H), 7.95 (d, 1H), 8.95 (s, 1H), 9.25 (s, 1H); m/z: (ES+) 380.4 (MH+).

Workup

  1. customwas partitioned between EtOAc and water
  2. washThe organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated at reduced pressure
  5. customThe residue was purified by chromatography (0.1%NH3 (aq), 3–10% MeOH in DCM as eluent)
  6. customUpon evaporation of the fractions
  7. customobtained,this was triturated with ether

Sources & evidence

ORD record
ord-13cbe94dd84b4283a8dfc0f879c51fc9
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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