Ammonia → 1-Bromo-3-cyclobutylimidazo[1,5-a]pyrazin-8-amine

HRID 1163248Notes

Reaction equation

[Br:1][C:2]1[N:3]=[C:4]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7](Cl)[C:6]=12.[NH3:16].O>CC(O)C>[Br:1][C:2]1[N:3]=[C:4]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH2:16])[C:6]=12

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 1-bromo-8-chloro-3-cyclobutylimidazo[1,5-a]pyrazine (341 mg, 1.2 mmol) in IPA (3 mL) was saturated with NH3(g) at 0° C. for 3 min. The tube was sealed and heated at 100° C. for 17 h. H2O (10 mL) was added and the mixture was extracted with EtOAc (3×30 mL). The organic phase was washed with brine and concentrated under reduced pressure to provide the title compound as a white solid; 1H NMR (400 MHz, CDCl3) δ 7.30 (d, J=4.8 Hz, 1H), 6.97 (d, J=5.2 Hz, 1H), 5.65 (br, 2H), 3.70 (qud, J=0.8 Hz, 8.4 Hz, 1H), 2.55-2.35 (m, 4H), 2.18-1.93 (m, 2H); MS (ES+): m/z 267.1 (100), 269.1 (100) [MH+]; HPLC: tR=1.70 min (OpenLynx, polar—5 min).

Workup

customThe tube was sealed
extractionthe mixture was extracted with EtOAc (3×30 mL)
washThe organic phase was washed with brine
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-7ed3d395572c4fd69ea3341bc7f267c3
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820662B2

Reaction notes

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