Sodium Hydroxide → HCID 21104325, compound

HRID 1010852Notes

Reaction equation

HRID 1010852 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 1 N 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 r.t. 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-fe3dcb45c4f04b4da96dc0d565377fec
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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