Hydrochloric Acid → HCID 178518399, compound

HRID 1666666Notes

Reaction equation

HRID 1666666 reaction equation
Cl.C[C:3]1[S:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8](O)=[O:9].[NH2:12][C:13](N)=[O:14].[OH-].[Na+].Cl>>[N:11]1[C:6]2=[CH:5][S:4][CH:3]=[C:7]2[C:8]([OH:9])=[N:12][C:13]=1[OH:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 14798Sodium HydroxideHCID 67793993HCID 67793993, compound

Product 1

HCID 178518399HCID 178518399, compoundYield 115.1%

Conditions

Temperature
180 °C

Procedure

A mixture of methyl 4-aminothiophene-3-carboxylic acid mono hydrochloride (1.00 g) and urea (1.8 g) was stirred at 180° C. for 1.5 h. The mixture was left stand for cooling to room temperature, followed by addition of 1 M aqueous sodium hydroxide to dissolve the solids, and the mixture was neutralized with 1 M hydrochloric acid. The precipitated crystals were collected by filtration to obtain thieno[3,4-d]pyrimidine-2,4-diol (1.0 g). (2) To a mixture of thieno[3,4-d]pyrimidine-2,4-diol (1.00 g) and phosphorus oxychloride (10 mL) was added N,N-dimethylaniline (2.0 mL) at room temperature, and the mixture was stirred at 100° C. for 2.5 h. The reaction solution was added dropwise to water (30 g) with ice cooling, and the aqueous layer was extracted with chloroform. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel, chloroform) to obtain 2,4-dichlorothieno[3,4-d]pyrimidine (0.52 g).

Workup

  1. waitThe mixture was left stand
  2. temperaturefor cooling to room temperature
  3. dissolutionto dissolve the solids
  4. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-7415f27bb7af45d0ad33dfb2b500234d
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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