Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloride | HCID 312 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (R)-4-(6-Methoxyquinazolin-2-yl)-4-methyloxazolidin-2-one | HCID 67408275 | — |
| Product | HCID 67408663 | HCID 67408663 | — |
Reaction Steps
(R)-4-(6-Methoxy-quinazolin-2-yl)-4-methyl-oxazolidin-2-one (860.0 mg, 3.317 mmol) was dissolved in methylene chloride (60 mL, 900 mmol), and cooled to −78° C. A solution of 1.0 M of boron tribromide in nethylene chloride (9.95 mL, 9.95 mmol) was then added dropwise. The reaction mixture was then warmed up to at 23° C. gradually and then heated at 50° C. for 2 hours. The reaction mixture was then question with NaHCO3 (sat) to basic, and neutralized back to pH-7-8. DCM was removed under vacuum, the white solid was collected and washed with water and hexanes (560 mg, 69%). 1H NMR (MeOD) δ: 9.32 (s, 1H), 7.91 (d, J=9.3 Hz, 1H), 7.57 (dd, J=9.0, 2.8 Hz, 1H), 7.26 (d, J=2.5 Hz, 1H), 4.98 (d, J=8.5 Hz, 1H), 4.46 (d, J=8.5 Hz, 1H), 1.78 (s, 3H). MS (M+1): 246.10.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09181191B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-ddcbc06cf1004b24bc09c6e8085af7b1 |
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| Source note | uspto-grants-2015_11 |
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