Sodium Hydroxide → HCID 21104327, compound

HRID 1354337Notes

Reaction equation

HRID 1354337 reaction equation
C([O:3][C:4](=[O:30])[C:5]1[C:10]([NH:11][C:12]2[C:17]3[CH:18]([CH3:21])[CH2:19][CH2:20][C:16]=3[N:15]=[C:14]([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=3[F:29])[N:13]=2)=[CH:9][CH:8]=[N:7][CH:6]=1)C.[OH-].[Na+]>CO>[Cl:28][C:26]1[CH:25]=[CH:24][C:23]([F:29])=[C:22]([C:14]2[N:13]=[C:12]([NH:11][C:10]3[C:5]([C:4]([OH:30])=[O:3])=[CH:6][N:7]=[CH:8][CH:9]=3)[C:17]3[CH:18]([CH3:21])[CH2:19][CH2:20][C:16]=3[N:15]=2)[CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58865978HCID 58865978, compound

Product 1

HCID 21104327HCID 21104327, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-[2-(5-chloro-2-fluoro-phenyl)-5-methyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-nicotinic acid ethyl ester (180 mg, 0.42 mmol, 1 eq) in MeOH (5 ml) was added a 1N NaOH(aq) solution (634 μl, 0.63 mmol, 1.5 eq) and the reaction mixture was heated to reflux for 1 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 give 4-[2-(5-chloro-2-fluorophenyl)-5-methyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-nicotinic acid, 49 (160 mg, 95%) as a white solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1 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-a83902011de14defab3d46dcc540a490
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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