Tetrahydrofuran → HCID 178428239, compound

HRID 473990Notes

Reaction equation

HRID 473990 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[N:16]=[C:15]([N:17]3[CH2:20][CH2:19][CH2:18]3)[CH:14]=[C:13]([NH:21][C:22]3[NH:23][N:24]=[C:25]([CH3:27])[CH:26]=3)[N:12]=2)=[CH:6][CH:5]=1.[OH-].[Na+].O1CCCC1>CO>[N:17]1([C:15]2[CH:14]=[C:13]([NH:21][C:22]3[NH:23][N:24]=[C:25]([CH3:27])[CH:26]=3)[N:12]=[C:11]([S:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:28])=[O:2])=[CH:5][CH:6]=3)[N:16]=2)[CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 1784983204-[4-azetidin-1-yl-6-(5-methyl-2H-pyrazol-3-ylamino)-pyrimidin-2-ylsulfanyl]-benzoic acid methyl ester

Product 1

HCID 178428239HCID 178428239, compoundYield 109.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 50 ml round bottom flask equipped with a condenser was charged with 4-[4-azetidin-1-yl-6-(5-methyl-2H-pyrazol-3-ylamino)-pyrimidin-2-ylsulfanyl]-benzoic acid methyl ester (800 mg, 2.0 mmol), 2M sodium hydroxide aqueous solution (5 ml), tetrahydrofuran (30 ml) and methanol (5 ml). The reaction mixture was heated to reflux for one hour. The reaction mixture was allowed to cool to room temperature and concentrated in vacuo. The solid residue was taken up in methanol (30 ml) and concentrated hydrochloric acid (1 ml). The solvent was then removed under reduced pressure to give the title compound (0.84 g, 100%) as a mono HCl salt. 1H NMR (DMSO) 2.05-2.10 (3H, s), 2.20-2.30 (2H, m), 3.80-3.85 (2H, t), 4.05-4.10 (2H, s), 7.40-7.45 (2H, d), 7.85-7.90 (2H, d). MS (ES+): 383

Workup

  1. customA 50 ml round bottom flask equipped with a condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for one hour
  4. concentrationconcentrated in vacuo
  5. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-c417edad822d48a88b4a36e1ec232bde
Source dataset
uspto-grants-2014_01
Patent number
US08637511B2

Reaction notes

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