Sodium Hydroxide → HCID 59468537, compound

HRID 1012197Notes

Reaction equation

HRID 1012197 reaction equation
OCC(CO)(C)C[O:5][C:6](=[O:28])[CH2:7][C:8]1[S:9][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[CH:21]=3)[N:14]=2)=[CH:11][CH:12]=1.[OH-].[Na+]>C1COCC1>[OH:27][CH2:26][C:22]1[CH:21]=[C:20]([NH:19][C:15]2[N:14]=[C:13]([C:10]3[S:9][C:8]([CH2:7][C:6]([OH:28])=[O:5])=[CH:12][CH:11]=3)[CH:18]=[CH:17][N:16]=2)[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59468619HCID 59468619, compound

Product 1

HCID 59468537HCID 59468537, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{5-[2-(3-Hydroxymethyl-phenylamino)-pyrimidin-4-yl]-thiophen-2-yl}-acetic acid 3-hydroxy-2-hydroxymethyl-2-methyl-propyl ester (717 mg, 1.6 mmol) was dissolved in 30 mL of THF and 1N sodium hydroxide solution (3.5 mL, 3.5 mmol). The mixture was stirred overnight, quenched with acetic acid, and concentrated. The crude product was triturated with water to give 496 mg of {5-[2-(3-Hydroxymethyl-phenylamino)-pyrimidin-4-yl]-thiophen-2-yl}-acetic acid as an orange solid (1.45 mmol, 90%).

Workup

  1. customquenched with acetic acid
  2. concentrationconcentrated
  3. customThe crude product was triturated with water

Sources & evidence

ORD record
ord-4f73bc9d6fec4b61a9d6e675107a534f
Source dataset
uspto-grants-2011_07
Patent number
US07977481B2

Reaction notes

Loading…