Sodium Hydroxide → HCID 178435039, compound

HRID 471469

Reaction equation

HRID 471469 reaction equation
[C:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[S:5][C:4]=1[NH:10][C:11]([NH:13]C(=O)C1C=CC=CC=1)=[O:12])#[N:2].[OH-].[Na+]>CCO>[NH2:2][C:1]1[C:3]2[C:7]([CH3:8])=[C:6]([CH3:9])[S:5][C:4]=2[NH:10][C:11](=[O:12])[N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57456902N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide

Product 1

HCID 178435039HCID 178435039, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide (example 4a) (44.35 g, 148.1 mmol) and NaOH (2 N, 204 mL) in EtOH (400 mL) was stirred at 100° C. under nitrogen for four hours. The clear reaction solution was filtered and the filtrate was cooling to room temperature, and then was carefully neutralized with 10% AcOH (˜120 mL) with vigorous stirring at 0° C. After stirring overnight from 0° C. to room temperature, the resultant precipitate was collected by filtration, washed with warm water (60-70° C., 150 mL×4) and 20% EtOH in water (200 mL×2), and then dried at 50° C. under vacuum overnight to give the final product 4-amino-5,6-dimethylthieno[2,3-d]pyrimidin-2(1H)-one (27.7 g, 96%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.98 (brs, 1H), 2.24 (s, 3H), 2.19 (s, 3H). MS 196 (MH+).

Workup

  1. filtrationThe clear reaction solution was filtered
  2. stirringAfter stirring overnight from 0° C. to room temperature
  3. filtrationthe resultant precipitate was collected by filtration
  4. washwashed with warm water (60-70° C., 150 mL×4) and 20% EtOH in water (200 mL×2)
  5. customdried at 50° C. under vacuum overnight

Sources & evidence

ORD record
ord-4f21739ed6234c16b8934ed63d420269
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Linked notes

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