Boron tribromide → HCID 44633327, compound

HRID 1027477Notes

Reaction equation

B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([C:13]2[O:14][C:15]3[N:16]=[C:17]([CH2:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[N:18]=[C:19]([O:22][CH2:23][CH2:24][CH3:25])[C:20]=3[N:21]=2)[CH:10]=[CH:11][CH:12]=1.C(=O)([O-])O.[Na+]>ClCCl>[N:27]1([CH2:26][C:17]2[N:18]=[C:19]([O:22][CH2:23][CH2:24][CH3:25])[C:20]3[N:21]=[C:13]([C:9]4[CH:8]=[C:7]([OH:6])[CH:12]=[CH:11][CH:10]=4)[O:14][C:15]=3[N:16]=2)[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1

Participants

Conditions

Temperature: 0 °C

Procedure

1.25 ml of a 1 M solution of boron tribromide in dichloromethane were slowly added to a solution of 160 mg of 2-(3-methoxy-phenyl)-5-morpholin-4-ylmethyl-7-propoxy-oxazolo[5,4-d]pyrimidine in 5 ml of dichloromethane at 0° C. The reaction mixture was stirred at 0° C. for 2 h and at room temperature for 1 h. The mixture was cautiously neutralized with a saturated solution of sodium hydrogencarbonate. The organic layer was separated and the aqueous layer extracted two times with dichloromethane. The combined organic layers were dried with sodium sulfate, filtered and evaporated in vacuo. The residue was purified by preparative HPLC (method HPLC1) to give 23 mg of the title compound in the form of 3-(5-morpholin-4-ylmethyl-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)phenol trifluoroacetic acid salt.

Workup

customThe organic layer was separated
extractionthe aqueous layer extracted two times with dichloromethane
dry with materialThe combined organic layers were dried with sodium sulfate
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by preparative HPLC (method HPLC1)

Sources & evidence

ORD record: ord-4a559d65bc074872a74cf7fe689b90de
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735387B2

Reaction notes

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