3-Bromoaniline → Benzofurano[3,2-d]pyrimidine deriv. 77

HRID 1489622Notes

Reaction equation

HRID 1489622 reaction equation
Cl[C:2]1[C:3]2[O:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[C:4]=2[N:5]=[CH:6][N:7]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>C(OCCO)C>[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH:19][C:2]1[C:3]2[O:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 6092956-Chloro-8-oxa-3,5-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),3,5,10,12-hexaene

Product 1

HCID 5328425Benzofurano[3,2-d]pyrimidine deriv. 77Yield 8.1%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 4-chlorobenzofurano[3,2-d]pyrimidine (116mg, 0.57 mmol) and 3-bromoaniline (0.07 mL, 0.6 mmol) is heated at 135° C. under N2 in stirred 2-ethoxyethanol for 3 h. The mixture precipitates upon cooling, and the solid is collected and recrystallized from EtOH to give 4-(3-bromoanilino)benzofurano[3,2-d]pyrimidine (15.7 mg, 8%). 1H NMR (DMSO) δ10.35 (1H, s), 8.73 (1H, s), 8.34 (1H, t, J=1.9 Hz), 8.17 (1H, ddd, J=7.2, 1.2, 0.7 Hz), 7.93 (1H, ddd, J=8.2, 2.2, 1.0 Hz), 7.88 (1H, d, J=8.4 Hz), 7.77 (1H, dt, Jd =1.4 Hz, Jt =7.2 Hz), 7.56 (1H, dt, Jd =0.8 Hz, Jt =8.0 Hz), 7.34 (1H, t, J=8.0 Hz), 7.27 (1H, ddd, J=8.0, 2.0, 1.0 Hz).

Workup

  1. customThe mixture precipitates
  2. temperatureupon cooling
  3. customthe solid is collected
  4. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-d4cc511fd037494489cbc949fa427309
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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