HCID 68453426, compound → HCID 59924695, compound

HRID 2300830Notes

Reaction equation

HRID 2300830 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14](Cl)[CH:13]=[C:12]([CH3:17])[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].[N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[NH:21][CH:20]=1>CN(C=O)C>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]=[CH:20]3)[CH:13]=[C:12]([CH3:17])[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 68453426HCID 68453426, compoundHCID 86758757HCID 86758757, compound

Product 1

HCID 59924695HCID 59924695, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-[(S)-1-phenylethylamino]-4-chloro-6-methylpyrimidine (11 mg, 0.044 mmol, 1 eq) in DMF (0.2 mL) was added a solution of benzimidazole sodium salt (0.088 mL of a 1M solution, 0.088 mmol, 2 eq). The mixture was warmed to 100° C. for 2 h. The mixture was cooled and the DMF was removed under reduced pressure. The residue was purified by preparative thin layer chromatography (eluted with 2:1 hexanes/acetone to give 9.9 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 1.23 (3H, d, J=7 Hz), 2.45 (3H, s), 5.2 (1H br s), 5.62 (1H, br s), 6.6 (1H, s), 7.2-7.5 (7H, m), 7.8 (2H, d, J=8 Hz), 8.46 (1H, br s). Mass spectrum (NH3/CI): 330.1 (M+1).

Workup

  1. temperatureThe mixture was cooled
  2. customthe DMF was removed under reduced pressure
  3. customThe residue was purified by preparative thin layer chromatography (
  4. washeluted with 2:1 hexanes/acetone

Sources & evidence

ORD record
ord-950aaff55b434fa499734f155a1f5296
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

Loading…