Formic Acid → 5,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-one

HRID 1891024

Reaction equation

HRID 1891024 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]#[N:12].[CH:13](O)=O.Cl.[OH2:17]>>[N:1]1[C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=3[C:3]=2[C:11](=[O:17])[NH:12][CH:13]=1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 783822-Amino-4,5,6,7-tetrahydrobenzo(b)thiophene-3-carbonitrile

Product 1

HCID 986145,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-oneYield 77%

Procedure

To a mixture of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl cyanide (0.9 g) and formic acid (10 mL) was added 0.1 mL conc. HCl. After refluxed for 16 h, the reaction mixture was cooled and water (20 mL) was added. The precipitate was collected by filtration and washed thoroughly with water and hexanes to give the title compound (0.8 g, 77%). 1H NMR (300 MHz, CDCl3): δ 7.91 (s, 1H), 3.03-3.00 (m, 2H), 2.80-2.77 (m, 2H), 1.89-1.83 (m, 4H).

Workup

  1. temperatureAfter refluxed for 16 h
  2. temperaturethe reaction mixture was cooled
  3. filtrationThe precipitate was collected by filtration
  4. washwashed thoroughly with water and hexanes

Sources & evidence

ORD record
ord-0503b9880e4945daaed7066ffffc3269
Source dataset
uspto-grants-2013_08
Patent number
US08507502B2

Linked notes

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