Ammonia → HCID 69198722, compound

HRID 750819Notes

Reaction equation

HRID 750819 reaction equation
[NH3:1].CS([C:6]1[N:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[C:9]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[C:8]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[N:7]=1)(=O)=O>C1COCC1>[NH2:1][C:6]1[N:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[C:9]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[C:8]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10392549HCID 10392549, compound

Product 1

HCID 69198722HCID 69198722, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 5 mL round bottom flask fitted with a magnetic stir bar and rubber septum was added 1 mL THF and excess ammonia gas. The flask was cooled to 0°. 2-(methylsulfonyl)-4-(3,4-difluorophenoxy)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]pyrimidine (Example 20, 270 mg, 0.5 mmol) was added. The reaction mixture was stirred overnight at room temperature. The reaction mixture was washed with saturated NaHCO3, dried over MgSO4, filtered and the solvent removed under reduced pressure. Flash column chromatography on silica gel (eluted with 60/40 hexanes/ethyl acetate) afforded 2-(amino)-4-(3,4-difluorophenoxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine. HPLC/MS: m/e=480 (M+1); Rt=4.2 min; 1H-NMR 500 MHz (CD3OD): δ 6.95 (m, 1H), 7.20 (m, 4H), 7.28 (m, 4H), 7.41 (d, J=2 Hz, 1H).

Workup

  1. customTo a 5 mL round bottom flask fitted with a magnetic stir bar
  2. temperatureThe flask was cooled to 0°
  3. washThe reaction mixture was washed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-f558ff000ab4450699e2e083d2689462
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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