Boron tribromide → HCID 66826635, compound

HRID 1468615Notes

Reaction equation

[NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH3:14])[C:12](=[O:15])[N:11]([CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][N:21]([C:24]5[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33]C)=[CH:26][CH:25]=5)[CH2:20][CH2:19]4)[CH:8]3[N:9]=2)=[C:5]([C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)[N:4]=[CH:3]1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH3:14])[C:12](=[O:15])[N:11]([CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][N:21]([C:24]5[CH:25]=[CH:26][C:27]([O:30][CH2:31][CH2:32][OH:33])=[CH:28][CH:29]=5)[CH2:20][CH2:19]4)[CH:8]3[N:9]=2)=[C:5]([C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)[N:4]=[CH:3]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of compound 5-amino-8-(2-furyl)-3-[2-[4-[4-(2-methoxyethoxy)phenyl]piperazin-1-yl]ethyl]-1-methyl-[1,2,4]triazolo[5,1-f]purin-2-one (Example A1) (0.075 g, 0.140 mmol), in DCM (10 ml) was added BBr3 (0.15 ml, 0.154 mmol) drop wise at 0° C. and stirred at 25° C. for 20 hours. The reaction mixture was quenched with sat. NaHCO3 (25 ml) and extracted with DCM (3×20 ml). The crude product was purified by column chromatography to obtain 5-amino-8-(2-furyl)-3-[2-[4-[4-(2-hydroxyethoxy)phenyl]piperazin-1-yl]ethyl]-1-methyl-[1,2,4]triazolo[5,1-f]purin-2-one (70 mg, 90%) as an off white solid

Workup

customThe reaction mixture was quenched with sat. NaHCO3 (25 ml)
extractionextracted with DCM (3×20 ml)
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-3e5062cd288a403c80904c247150d094
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006177B2

Reaction notes

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