Sodium Hydroxide → 4-[2-(5-Chloro-2-fluorophenyl)-6,7-dihydrofuro[3,2-d]pyrimidin-4-ylamino]-nicotinic acid

HRID 1010865Notes

Reaction equation

HRID 1010865 reaction equation
C([O:3][C:4](=[O:29])[C:5]1[C:10]([NH:11][C:12]2[C:13]3[O:28][CH2:27][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[O:28][CH2:27][CH2:26][C:14]=3[N:15]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 588660344-[2-(5-Chloro-2-fluorophenyl)-6,7-dihydrofuro[3,2-d]pyrimidin-4-ylamino]-nicotinic acid ethyl ester

Product 1

HCID 211043304-[2-(5-Chloro-2-fluorophenyl)-6,7-dihydrofuro[3,2-d]pyrimidin-4-ylamino]-nicotinic acidYield 94.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-[2-(5-chloro-2-fluorophenyl)-6,7-dihydrofuro[3,2-d]pyrimidin-4-ylamino]-nicotinic acid ethyl ester (100 mg, 0.24 mmol, 1 eq) in MeOH (5 ml) was added a 1 N NaOH(aq) solution (290 μl, 0.29 mmol, 1.2 eq) and the reaction mixture was refluxed for 5 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-fluorophenyl)-6,7-dihydrofuro[3,2-d]pyrimidin-4-ylamino]-nicotinic acid (88 mg, 94%) as a cream colored solid.

Workup

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

Sources & evidence

ORD record
ord-bd2301a8c8544d4cb50074a53bb0324b
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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