HCID 18186484, compound → HCID 18186489, compound

HRID 1357547Notes

Reaction equation

HRID 1357547 reaction equation
[NH:1]([C:8]1[C:13]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][N:11]=[C:10]([Cl:22])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C>[NH:1]([C:8]1[C:13]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][N:11]=[C:10]([Cl:22])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 18186484HCID 18186484, compound

Product 1

HCID 18186489HCID 18186489, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Anilino-2-chloro-5-(2-phenylethynyl)pyrimidine (Method 72; 400 mg) was dissolved in ethyl acetate (100 ml) and the solution was purged with nitrogen. 5% Rhodium on carbon (50 mg) was added and the mixture was hydrogenated at standard temperature and pressure (STP) for 20 hours. A further portion of 5% rhodium on carbon catalyst (50 mg) was added and the solution was hydrogenated at STP for a further 3 hours. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by bond elute chromatography, eluting with 0-10% ethyl acetate in isohexane, to give the product (70 mg). NMR (CDCl3): 2.8 (t, 2H), 3.0 (t, 2H), 6.25 (s, 1H), 7.1 (m, 1H), 7.15-7.4 (m, 9H), 7.95 (s, 1H); MS (MH+): 310, 312.

Workup

  1. customthe solution was purged with nitrogen
  2. addition5% Rhodium on carbon (50 mg) was added
  3. additionA further portion of 5% rhodium on carbon catalyst (50 mg) was added
  4. waitthe solution was hydrogenated at STP for a further 3 hours
  5. customThe catalyst was removed by filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by bond
  8. washelute chromatography
  9. washeluting with 0-10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-dacf23c6899a47b8993b740be6fa6090
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

Loading…