4-Aminobenzylamine → (4-Aminobenzyl)-(5,6-diphenylfuro[2,3-d]pyrimidin-4-yl)amine

HRID 1095468Notes

Reaction equation

HRID 1095468 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:23][CH2:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1>C(O)CCC>[NH2:29][C:28]1[CH:30]=[CH:31][C:25]([CH2:24][NH:23][C:2]2[C:3]3[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[C:9]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[O:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 4278144-AminobenzylamineHCID 11449637HCID 11449637, compound

Product 1

HCID 46855199(4-Aminobenzyl)-(5,6-diphenylfuro[2,3-d]pyrimidin-4-yl)amineYield 70.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Chloro-5,6-diphenylfuro[2,3-d]pyrimidine (0.10 g) and 4-(aminomethyl)aniline (0.05 g) in n-butanol (5 mL) were heated at 80° C. for 16 h. The reaction mixture was concentrated and the residue was partitioned between water and ethyl acetate. The organic layer was concentrated and the residue was purified by silica gel column chromatography using a mixture of dichloromethane:methanol (40:1), to give N-(4-aminobenzyl)-5,6-diphenylfuro[2,3-d]pyrimidin-4-amine (0.09 g, 70%). 1H NMR (300 MHz, CDCl3): δ 8.44 (s, 1H), 7.54-7.44 (m, 8H), 7.27-7.25 (m, 2H), 6.93 (d, 2H), 6.10 (d, 2H), 4.87 (t, 1H), 4.51 (d, 2H), 3.65 (brs, 2H). LC-MS (ESI) m/z 393.7 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between water and ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by silica gel column chromatography
  5. additiona mixture of dichloromethane:methanol (40:1)

Sources & evidence

ORD record
ord-5623c00622e8444c9460cc557867bf07
Source dataset
uspto-grants-2012_03
Patent number
US08138194B2

Reaction notes

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