Dimethylformamide → HCID 135427949, compound

HRID 556412Notes

Reaction equation

HRID 556412 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[S:23][C:11]2=[N:12][C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][C:15]([CH3:16])=[C:10]2[C:9]=1[NH:24][C:25]([NH:27]C(=O)C1C=CC=CC=1)=[S:26])=O)C.CN(C)C=O.I[CH2:42][CH3:43]>C(O)C>[CH2:42]([S:26][C:25]1[NH:27][C:6](=[O:5])[C:8]2[S:23][C:11]3[N:12]=[C:13]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:14]=[C:15]([CH3:16])[C:10]=3[C:9]=2[N:24]=1)[CH3:43]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 14798Sodium Hydroxide2×HCID 57503715HCID 57503715, compound

Product 1

HCID 135427949HCID 135427949, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.5 ml (10.5 mmol) 1 M sodium hydroxide solution is added to 2.00 g (4.2 mmol) 3-(3-benzoylthioureido)-4-methyl-6-phenyl-thieno[2,3-b]-pyridine-2-carboxylic acid ethyl ester in 25 ml ethanol and refluxed for 30 min. Following the addition of 10 ml N,N-dimethylformamide, 5 ml (5 mmol) sodium hydroxide solution (1M) and 0.50 ml iodoethane (6.2 mmol) the next step is stirring at room temperature for 30 min. The precipitate precipitated following acidification with dilute hydrochloric acid is sucked off, washed with water, suck dried and dried in vacuo at 50° C. 1.23 g (83%) 2-ethylthio-9-methyl-7-phenyl-pyrido[3′,2′:4,5]thieno-[3,2-d]pyrimidin-4-one is obtained.

Workup

  1. temperaturerefluxed for 30 min
  2. customThe precipitate precipitated
  3. washwashed with water, suck
  4. customdried
  5. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-b91726d959404f9c9a8f009666ddecd8
Source dataset
uspto-grants-2011_11
Patent number
US08058285B2

Reaction notes

Loading…