Pyridine → HCID 57708889, compound

HRID 606501Notes

Reaction equation

HRID 606501 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][CH2:12][C:13]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([C:23]([OH:25])=[O:24])=[N:17][C:16]=3[S:15][CH:14]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[C:26](Cl)(=O)[C:27](Cl)=O.N1C=CC=[CH:34][CH:33]=1>CN(C=O)C.C1COCC1>[CH2:33]([O:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][CH2:12][C:13]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:17][C:16]=3[S:15][CH:14]=2)=[CH:6][CH:5]=1)=[O:3])[CH3:34]

Participants

6

Reactant 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 59652252HCID 59652252, compound

Product 1

HCID 57708889HCID 57708889, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-({[(4-carboxyphenyl)methyl]oxy}methyl)-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylic acid (2.88 g, 7.99 mmol) and THF (30 mL) were added oxalyl chloride (4.60 mL, 52.7 mmol) and DMF (one drop), and the mixture was stirred at room temperature for 1 hr, and concentrated. THE (15 mL) and ethanol (15 mL) were added to the residue. Pyridine (5.69 mL, 70.3 mmol) was added to the mixture, and the mixture was stirred at room temperature for 12 hr, and concentrated under reduced pressure. Ethyl acetate and 1N hydrochloric acid were added to the residue, and the precipitated solid was collected by filtration, and washed with 1N hydrochloric acid (×2), water (×4) and diethyl ether (×1). The obtained crude crystals were recrystallized from THF-ethyl acetate to give the title compound as a white powder (1.87 g, 56%).

Workup

  1. concentrationconcentrated
  2. additionTHE (15 mL) and ethanol (15 mL) were added to the residue
  3. stirringthe mixture was stirred at room temperature for 12 hr
  4. concentrationconcentrated under reduced pressure
  5. additionEthyl acetate and 1N hydrochloric acid were added to the residue
  6. filtrationthe precipitated solid was collected by filtration
  7. washwashed with 1N hydrochloric acid (×2), water (×4) and diethyl ether (×1)
  8. customThe obtained crude crystals
  9. customwere recrystallized from THF-ethyl acetate

Sources & evidence

ORD record
ord-5bbd104cfb69488b8d2697e88b212696
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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