Benzylamine → HCID 814517, compound

HRID 1489604Notes

Reaction equation

HRID 1489604 reaction equation
Cl.Cl[C:3]1[C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[N:6]=[CH:7][N:8]=1.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCOC(C)=O>[CH2:16]([NH:23][C:3]1[C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[N:6]=[CH:7][N:8]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 181843684-Chloro-5H-pyrimido[5,4-b]indole--hydrogen chloride (1/1)

Product 1

HCID 814517HCID 814517, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Chloroindolo[3,2-d]pyrimidine hydrochloride (240 mg, 1 mmol, and benzylamine (1 mL) are stirred under a dry nitrogen atmosphere at 150 C. for 6 hours, and then concentrated under reduced pressure to give an oily soft solid which is dissolved in EtOAc (20 mL), and washed with saturated sodium bicarbonate solution (20 mL), water (3×15 mL), and brine (20 mL). The solution is dried (MgSO4) and the solvent is removed under reduced pressure. Trituration of the residue with dichloromethane, gives 4-benzylaminoindolo[3,2-d]pyrimidine (190 mg, 69%). 1H NMR (CDCl3): δ10.58 (1H, brs), 8.60 (1H, s), 8.08 (1H, d, J=8.0 Hz), 7.47-7.14 (8H, m), 4.82 (2H, d, J=5.6 Hz), 2.41 (1H, brs).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give an oily soft solid which
  3. washwashed with saturated sodium bicarbonate solution (20 mL), water (3×15 mL), and brine (20 mL)
  4. dry with materialThe solution is dried (MgSO4)
  5. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-72064c487e364658a8db627539795ab1
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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