3-Bromoaniline → N-(3-Bromophenyl)thieno[3,2-d]pyrimidin-4-amine hydrochloride

HRID 1059639Notes

Reaction equation

HRID 1059639 reaction equation
[Cl:1][C:2]1[C:3]2[S:10][CH:9]=[CH: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[S:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 27358214-Chlorothieno[3,2-d]pyrimidine

Product 1

HCID 22736818N-(3-Bromophenyl)thieno[3,2-d]pyrimidin-4-amine hydrochlorideYield 72.2%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
79 °C

Procedure

A mixture of 4-chlorothieno(3,2-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. The resulting precipitate is filtered and washed with CH2Cl2 to yield 4-(3-bromo-anilino)thieno[3,2-d]pyrimidine hydrochloride (195.5 mg, 72%) a s a light yellow solid. 1H NMR (DMSO) δ 11.33 (1H, s), 8.94 (1H, s), 8.23 (1H, s), 8.53 (1H, d, J=5.3 Hz), 8.07 (1H, s), 7.77 (1H, d, J=7.9 Hz), 7.6 (1H, d, J=5.3 Hz), 7.48 (2H, m).

Workup

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

Sources & evidence

ORD record
ord-ed6ccf2b4ede450fbbebea207e23a805
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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