Sodium Hydroxide → HCID 21104325, compound

HRID 1354319Notes

Reaction equation

HRID 1354319 reaction equation
C([O:3][C:4](=[O:29])[C:5]1[C:10]([NH:11][C:12]2[C:13]3[CH2:28][O:27][CH2:26][C:14]=3[N:15]=[C:16]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[F:25])[N:17]=2)=[CH:9][CH:8]=[N:7][CH:6]=1)C.[OH-].[Na+]>CO>[Cl:24][C:22]1[CH:21]=[CH:20][C:19]([F:25])=[C:18]([C:16]2[N:17]=[C:12]([NH:11][C:10]3[C:5]([C:4]([OH:29])=[O:3])=[CH:6][N:7]=[CH:8][CH:9]=3)[C:13]3[CH2:28][O:27][CH2:26][C:14]=3[N:15]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58866010HCID 58866010, compound

Product 1

HCID 21104325HCID 21104325, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-[2-(5-chloro-2-fluoro-phenyl)-5,7-dihydro-furo[3,4-d]pyrimidin-4-ylamino]-nicotinic acid ethyl ester (60 mg, 0.14 mmol, 1 eq) in MeOH (5 ml) was added a 1N NaOH(aq) solution (300 μl, 0.30 mmol, 2 eq) and the reaction mixture was heated to reflux for 2 h. The solution was cooled to rt and concentrated in vacuo. Water (20 ml) was added to the crude material and the aqueous layer was acidified to pH 4. The solid was filtered, washed with water (2×5 ml) and dried overnight to afford 4-[2-(5-Chloro-2-fluoro-phenyl)-5,7-dihydro-furo[3,4-d]pyrimidin-4-ylamino]-nicotinic acid (50 mg, 90%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. additionWater (20 ml) was added to the crude material
  5. filtrationThe solid was filtered
  6. washwashed with water (2×5 ml)
  7. customdried overnight

Sources & evidence

ORD record
ord-fe61a4da08c0489bb988926191fd304f
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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