Tetrahydrofuran → HCID 178517813, compound

HRID 1056277Notes

Reaction equation

HRID 1056277 reaction equation
[OH-].[Na+].C1C[O:6]CC1.[Br:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([Cl:19])[N:15]=[C:14]2Cl>CC(O)=O>[Br:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([Cl:19])[N:15]=[C:14]2[OH:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 137858748-Bromo-2,4-dichloroquinazoline

Product 1

HCID 178517813HCID 178517813, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a biphasic mixture of NaOH 1 N aq. (10.79 mL, 10.79 mmol) and 11 mL THF was added 8-bromo-2,4-dichloroquinazoline (407b, 1.50 g, 5.40 mmol) in one portion. The reaction became dark red. After 20 min the reaction was checked by LC/MS and judged complete. The reaction was cooled in an ice/water bath and acidified with AcOH. The reaction was concentrated to ½ volume on rotovap (precipitate observed) and cooled in an ice/water bath. The slurry was filtered and the solid rinsed with 2× water. The orange solid was collected and dried in vacuo to give 8-bromo-2-chloroquinazolin-4-ol (1.10 g, 4.24 mmol, 79% yield) as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.49 (1H, br. s.), 8.15 (1H, dd, J=7.8, 1.4 Hz), 8.09 (1H, dd, J=7.9, 1.5 Hz), 7.45 (1H, t, J=7.8 Hz). m/z (ESI, +ve ion) 258.9/260.9 (M+H)+.

Workup

  1. temperatureThe reaction was cooled in an ice/water bath
  2. concentrationThe reaction was concentrated
  3. temperaturecooled in an ice/water bath
  4. filtrationThe slurry was filtered
  5. washthe solid rinsed with 2× water
  6. customThe orange solid was collected
  7. customdried in vacuo

Sources & evidence

ORD record
ord-568713646f6d484b8f08757795392085
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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