Chloride → HCID 67408663, compound

HRID 709884Notes

Reaction equation

HRID 709884 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C@:13]1([CH3:19])[CH2:17][O:16][C:15](=[O:18])[NH:14]1)[N:7]=[CH:6]2.C(Cl)Cl.B(Br)(Br)Br.[Cl-].C([O-])(O)=O.[Na+]>>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C@:13]1([CH3:19])[CH2:17][O:16][C:15](=[O:18])[NH:14]1)[N:7]=[CH:6]2

Participants

6

Reactant 5

HCID 312ChlorideHCID 6344DichloromethaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67408275(R)-4-(6-Methoxyquinazolin-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67408663HCID 67408663, compound

Conditions

Temperature
-78 °C

Procedure

(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.

Workup

  1. temperatureThe reaction mixture was then warmed up to at 23° C. gradually
  2. temperatureheated at 50° C. for 2 hours
  3. customDCM was removed under vacuum
  4. customthe white solid was collected
  5. washwashed with water and hexanes (560 mg, 69%)

Sources & evidence

ORD record
ord-ddcbc06cf1004b24bc09c6e8085af7b1
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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