2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → HCID 15712517, compound

HRID 2081208Notes

Reaction equation

HRID 2081208 reaction equation
Br[C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:17][N:18]1CCCN(C)C1=O>>[CH3:11][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[C:17]#[N:18])[C:7]2[C:15](=[O:16])[NH:14][CH2:13][CH2:12][C:8]1=2

Participants

3

Reactant 2

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 15712506HCID 15712506, compound

Product 1

HCID 15712517HCID 15712517, compound

Procedure

A mixture of 6-bromo-2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (1.1 g) and cuprous cyanide (1.0 g) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone (30 ml) was heated at 180° for 24 h. The mixture was poured onto ice (ca. 500 ml) and ferric (III) chloride (20 g), and stirred for 1 h. It was then extracted with dichloromethane (3×300 ml), and the combined organic extracts were washed with water (2×300 ml) and concentrated in vacuo. The residue was triturated with hexane (250 ml) followed by a mixture of ether/hexane (50:50; 100 ml) and finally with ether (60 ml) to give the title compound (620 mg), m.p. 230°-231°.

Workup

  1. temperaturewas heated at 180° for 24 h
  2. extractionIt was then extracted with dichloromethane (3×300 ml)
  3. washthe combined organic extracts were washed with water (2×300 ml)
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with hexane (250 ml)
  6. additionfollowed by a mixture of ether/hexane (50:50; 100 ml) and finally with ether (60 ml)

Sources & evidence

ORD record
ord-ac51dac7cb9d4c76a1fb952f7a260cd4
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

Loading…