Tetraethyl orthocarbonate → 4-(6-Bromo-2-ethoxy-1,3-benzodiazol-1-yl)pyrimidin-2-amine

HRID 1398641Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=1.[CH2:17]([O:19][C:20](OCC)(OCC)OCC)[CH3:18]>C(O)(=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:20]([O:19][CH2:17][CH3:18])[N:9]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=3)[C:3]=2[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine (652 mg, 1.98 mmol), (triethoxymethoxy)ethane (2.0 mL, 9.89 mmol) and acetic acid (0.09 mL) was heated at 80° C. for 40 minutes. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (5 mL) and washed with saturated aqueous sodium hydrogencarbonate (2×10 mL) and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give the crude product as an orange solid 1H NMR (500 MHz, CDCl3) delta 1.55 (3H, t, J=7.09 Hz), 4.71 (2H, q, J=7.25 Hz), 5.21 (2H, br. s.), 7.13 (1H, d, J=5.67 Hz), 7.35-7.42 (2H, m), 8.36-8.40 (2H, m); LC-MS: m/z=+334.00/335.75 (M+H)+.

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated in vacuo
dissolutionThe residue was dissolved in ethyl acetate (5 mL)
washwashed with saturated aqueous sodium hydrogencarbonate (2×10 mL)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-466ae22c45cc449099bda769b485e92d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901313B2

Reaction notes

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