Sodium Methoxide → HCID 136408153, compound

HRID 922387Notes

Reaction equation

HRID 922387 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][C:12]([F:20])=[CH:13][C:14]=3F)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:21][O-:22].[Na+]>CO>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][C:12]([F:20])=[CH:13][C:14]=3[O:22][CH3:21])[N:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 136408152HCID 136408152, compound

Product 1

HCID 136408153HCID 136408153, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2-(6-bromopyridin-2-yl)-5,7-difluoroquinazolin-4(3H)-one (12, 1.05 g, 3.11 mmol) and MeOH (15 mL) was added NaOMe (25% solution, 50 mL) at room temperature. After 24 hours, another portion of 25% NaOMe was added (25 mL). After an additional 48 hours at room temperature, the reaction was quenched with water and the pH adjusted to 7 with 2N HCl. The volume was reduced by half under reduced pressure and the remaining mixture was extracted with CH2Cl2 (3×250 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound (970 mg, 89%) as an off-white solid. 1H NMR (500 MHz, CDCl3) δ 10.56 (s, 1H), 8.57-8.43 (m, 1H), 7.79-7.74 (m, 1H), 7.71-7.62 (m, 1H), 7.09-6.99 (m, 1H), 6.71-6.65 (m, 1H), 4.02 (s, 3H).

Workup

  1. waitAfter an additional 48 hours at room temperature
  2. customthe reaction was quenched with water
  3. extractionthe remaining mixture was extracted with CH2Cl2 (3×250 mL)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-816c59d2f12c4c5193f2d5d91e62d71a
Source dataset
uspto-grants-2016_03
Patent number
US09278940B2

Reaction notes

Loading…