Urea → 6-(2,4-Difluoro-phenoxy)-1H-pyrido[3,4-d]pyrimidine-2,4-dione

HRID 457702Notes

Reaction equation

HRID 457702 reaction equation
CO[C:3](=[O:20])[C:4]1[C:9]([NH2:10])=[CH:8][N:7]=[C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])[CH:5]=1.[NH2:21][C:22](N)=[O:23]>O>[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[O:11][C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:22](=[O:23])[NH:21][C:3](=[O:20])[C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 588201935-Amino-2-(2,4-difluoro-phenoxy)-isonicotinic acid methyl ester

Product 1

HCID 184406256-(2,4-Difluoro-phenoxy)-1H-pyrido[3,4-d]pyrimidine-2,4-dioneYield 98.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound (1C) (4.2 g, 15.0 mmol) and urea (9.0 g, 10 eq) were heated to a melt at 160° C. with stirring. After 2 hours, the melt solidified and by TLC the reaction was complete. The reaction mixture was cooled to room temperature, water (250 mL) was added, and the resulting mixture was left to stand for 1 hour. Then the solids were broken up with a spatula and the mixture was stirred vigorously for 1 hour. After suction filtration, a tan powder was collected which was air-dried in the frit for two days. Drying under high vacuum at 56° C. gave the title compound (1D) as a tan powder (4.307 g, (M−H)−=290, M.P.>300° C.).

Workup

  1. waitthe resulting mixture was left
  2. waitto stand for 1 hour
  3. stirringthe mixture was stirred vigorously for 1 hour
  4. filtrationAfter suction filtration
  5. customa tan powder was collected which
  6. customwas air-dried in the frit for two days
  7. customDrying under high vacuum at 56° C.

Sources & evidence

ORD record
ord-b22efac00e8b497f82147eca830e8a3b
Source dataset
uspto-grants-2007_03
Patent number
US07189731B2

Reaction notes

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