3-Isocyanatopyridine → US9296747, Example 3

HRID 930502Notes

Reaction equation

HRID 930502 reaction equation
[C:1]1([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH2:17][NH:16][CH2:15][CH2:14][C:12]=3[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:18]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[C:19]=[O:20]>C(Cl)Cl>[NH:7]([C:8]1[N:9]=[CH:10][C:11]2[CH2:17][N:16]([C:19]([NH:18][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[O:20])[CH2:15][CH2:14][C:12]=2[N:13]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 27604933-IsocyanatopyridineHCID 104609480N-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Product 1

HCID 118970906US9296747, Example 3

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine, Intermediate 6 (75 mg, 0.33 mmol), 3-isocyanatopyridine (41.8 mg, 0.35 mmol) in CH2Cl2 (1.5 mL) was stirred at room temperature for 1 hour. After 1 hour the reaction mixture was diluted with CH2Cl2 and washed with sat. aqueous NaHCO3(aq). The organic phase was collected, dried and concentrated. The residue was dissolved in CH2Cl2 and washed with 3% aqueous LiCl solution and water. The organic phase was collected, dried and concentrated to give the title compound (45.9 mg).

Workup

  1. washwashed with sat. aqueous NaHCO3(aq)
  2. customThe organic phase was collected
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. washwashed with 3% aqueous LiCl solution and water
  7. customThe organic phase was collected
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8fb5bbed33ea4f298a56f5d494fdd45f
Source dataset
uspto-grants-2016_03
Patent number
US09296747B1

Reaction notes

Loading…