Boron tribromide → HCID 58338024, compound

HRID 1409288Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][NH:12][C:13]1[C:14]2[N:21]=[CH:20][S:19][C:15]=2[N:16]=[CH:17][N:18]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][NH:12][C:13]1[C:14]2[N:21]=[CH:20][S:19][C:15]=2[N:16]=[CH:17][N:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

[2-(2-Fluoro-4-methoxy-phenyl)-ethyl]-thiazolo[5,4-d]pyrimidin-7-ylamine (204 mg, 0.67 mmol) was dissolved in CH2Cl2 (3.4 mL) in a 25 mL round bottom flask equipped with a magnetic stir bar, a septum and a dry nitrogen line. After cooling to 0° C., the solution was treated with 1.0 M boron tribromide (BBr3) solution in CH2Cl2 (3.4 mL), and the reaction mixture became brown. After stirring 3 h at 0° C., the mixture was treated with satd aq sodium bicarbonate (NaHCO3; 10 mL) and stirred at 0° C. for another hour. The precipitate was collected by suction filtration, washed with cold H2O (2×5 mL), and air dried on the filter to provide 3-fluoro-4-[2-(thiazolo[5,4-d]pyrimidin-7-ylamino)-ethyl]phenol (Compound 58; 127 mg) as a beige powder: mp 193° C.; 1H NMR (DMSO-d6) δ 9.64 (br s, 1H), 9.24 (s, 1H), 8.42 (br m, 2H), 7.07 (t, J=8.8 Hz, 1H), 6.53-6.49 (m, 2H), 3.71-3.66 (m, 2H), 2.85 (t, J=7.3 Hz, 2H); ESIMS: m/z 291.2 ([M+H]+).

Workup

customequipped with a magnetic stir bar
stirringstirred at 0° C. for another hour
filtrationThe precipitate was collected by suction filtration
washwashed with cold H2O (2×5 mL), and air
customdried on the
filtrationfilter

Sources & evidence

ORD record: ord-4e90f78f079f4f5c830949b9de2fd39b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921382B2

Reaction notes

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