Potassium Carbonate → 4-Anilino-2-(4-(2,3-epoxypropoxy)anilino)pyrimidine

HRID 347757Notes

Reaction equation

HRID 347757 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]([OH:21])=[CH:17][CH:16]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:28]([CH:30]1[O:32][CH2:31]1)Br>CS(C)=O>[NH:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:28][CH:30]3[O:32][CH2:31]3)=[CH:19][CH:20]=2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 179811344-Anilino-2-(4-hydroxyanilino)pyrimidine

Product 1

HCID 179811334-Anilino-2-(4-(2,3-epoxypropoxy)anilino)pyrimidineYield 94.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Anilino-2-(4-hydroxyanilino)pyrimidine (Reference Example H-1, 0.541 g, 1.95 mmol) was dissolved in DMSO (2 ml) and treated with K2CO3 (0.537 g, 3.89 mmol) and epibromohydrin (0.33 ml, 0.53 g, 3.9 mmol). The reaction was allowed to stir at ambient temperature overnight. After warming to 40° C. for 5 hours the reaction was partitioned between EtOAc and water. The organic phase was washed four times with water, dried over MgSO4 and evaporated at reduced pressure. The residue was purified by chromatography (1–5% MeOH in DCM) to give the title product as an oil (0.614 g, 94%). NMR (300 MHz): 2.69 (m, 1H), 2.83 (m, 1H), 3.88 (m, 1H), 4.25 (m, 1H), 6.15 (d, 1H), 6.85 (d, 2H), 7.97 (t, 1H), 7.27 (t, 2H), 7.58 (d, 2H), 7.66 (d, 2H), 7.95 (d, 1H), 8.9 (s, 1H), 9.23 (s, 1H); m/z: (ES+) 335 (MH+).

Workup

  1. temperatureAfter warming to 40° C. for 5 hours the reaction
  2. customwas partitioned between EtOAc and water
  3. washThe organic phase was washed four times with water
  4. dry with materialdried over MgSO4
  5. customevaporated at reduced pressure
  6. customThe residue was purified by chromatography (1–5% MeOH in DCM)

Sources & evidence

ORD record
ord-9ad1248982714d11a5ca6ed47ed09c94
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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