Sodium Hydroxide → HCID 58788244, compound

HRID 2374747Notes

Reaction equation

HRID 2374747 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[N:16]([CH2:17][C:18]([O:20]CC)=[O:19])[C:15]2[CH:23]=[CH:24][S:25][C:14]=2[C:13](=[O:26])[N:12]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:15]2[CH:23]=[CH:24][S:25][C:14]=2[C:13](=[O:26])[N:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58788378HCID 58788378, compound

Product 1

HCID 58788244HCID 58788244, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-(2-[2-(2,3-difluorophenyl)ethyl]-4-oxo-4H-thieno[3,2-d]pyrimidin-1-yl)acetate (Int B57) (375 mg) as a suspension in dioxan (2-3 ml) was treated with 0.5M solution of aqueous sodium hydroxide (1.98 ml) at room temperature. After 1h the solution was concentrated to a small volume and acidified with 2M hydrochloric acid. The precipitate was filtered off, washed with water and dried in vacuo at 40° C. overnight. The title compound was obtained as a white solid (308 mgs, 89%); 1H-NMR (DMSO) δ 3.09 (4H, m), 5.19 (2H, s), 7.05-7.31 (3H, m), 7.49 (1H, d, J5.2 Hz) and 8.14 (1H, d, J5.2 Hz). (APCI+) Found (M+1)=351, C16H12F2N2O3S requires 350.

Workup

  1. concentrationAfter 1h the solution was concentrated to a small volume
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-c723bc3228554554adc2b5644531fa90
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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