3-Bromoaniline → HCID 22736821, compound

HRID 50849Notes

Reaction equation

HRID 50849 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>COCCO>[ClH:1].[Br:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH:15][C:2]1[C:3]2[CH:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 7366184-Chlorothieno[2,3-d]pyrimidine

Product 1

HCID 22736821HCID 22736821, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
79 °C

Procedure

A mixture of 4-chlorothieno[2,3-d]pyrimidine (135 mg, 0.79 mmol) and 3-bromoaniline (95 μL, 0.89 mmol) in 2-methoxyethanol (2 mL) is heated to 79° C. for 30 min with stirring. The resulting solid is filtered and washed with CH2Cl2 to yield 4-(3-bromoanilino)thieno[2,3-d]pyrimidine hydrochloride (197 mg, 73%). 1H NMR (DMSO) δ 9.99 (1H, s), 8.60 (1H, s), 8.23 (1H, s), 7.98 (1H, d, J=5.0 Hz), 7.88 (1H, d, J=8.0 Hz), 7.79 (1H, d, J=6.0 Hz), 7.37 (1H, t, J=8.0 Hz), 7.30 (1H, d, J=8.0 Hz).

Workup

  1. filtrationThe resulting solid is filtered
  2. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-eb20cb41350945148a672cbca293fd1f
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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