Hydrochloric Acid → HCID 11486614, compound

HRID 28584

Reaction equation

HRID 28584 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[O:15][CH2:16][CH3:17])[N:5]=[C:4]([NH2:18])[N:3]=1.C(O)C.Cl.[O:23]1[C:27]([C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)=[CH:26][N:25]=[CH:24]1>O1CCOCC1>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH2:16][CH3:17])=[C:8]([C:6]2[N:5]=[C:4]([NH2:18])[N:3]=[C:2]([NH:34][C:31]3[CH:30]=[CH:29][C:28]([C:27]4[O:23][CH:24]=[N:25][CH:26]=4)=[CH:33][CH:32]=3)[CH:7]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5177474-(1,3-Oxazol-5-yl)anilineHCID 860043254-Chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine

Product 1

HCID 11486614HCID 11486614, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 4-chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine (100 mg, 0.37 mmol) and ethanol (20 ml) was added a solution of hydrogen chloride in 1,4-dioxane (4 M, 0.1 ml). After stirring for 10 minutes, 4-oxazol-5-yl-phenyl-amine (60 mg, 0.37 mmol) was added and the mixture was heated under reflux for 5 hours. After concentrating under reduced pressure, the residue was stirred with ethyl acetate (10 ml) and saturated aqueous sodium bicarbonate solution (10 ml). The solid was filtered and purified by flash chromatography eluting with ethyl acetate-hexane (1:1 followed by 3:2) to yield the title compound (110 mg, 75% yield). 1H NMR (acetone-d6) δ 1.44 (t, 3H, J=7.0 Hz, CH3), 4.17 (q, 2H, J=7.0 Hz, CH2), 5.88 (br s, 2H, NH), 7.04 (s, 1H, Ar), 7.12 (d, 1H, J=8.5 Hz, Ar), 7.37 (dd, 1H, J=8.8 Hz, J=2.9 Hz, Ar), 7.46 (s, 1H, Ar), 7.68 (d, 2H, J=8.7 Hz, Ar), 7.88-7.91 (m, 2H, Ar), 8.07 (d, 1H, J=2.8 Hz, Ar), 8.16 (s, 1H, Ar), 8.64 (br s, 1H, NH).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. concentrationAfter concentrating under reduced pressure
  4. stirringthe residue was stirred with ethyl acetate (10 ml) and saturated aqueous sodium bicarbonate solution (10 ml)
  5. filtrationThe solid was filtered
  6. custompurified by flash chromatography
  7. washeluting with ethyl acetate-hexane (1:1 followed by 3:2)

Sources & evidence

ORD record
ord-0a3f7d8513d24223b65530e0dd37c1e1
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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