Triethylamine → HCID 22674414, compound

HRID 1005719Notes

Reaction equation

HRID 1005719 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[C:9]2[S:19][CH:18]=[CH:17][C:10]=2[N:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1)=[O:7].O=S(Cl)Cl.CCN(CC)CC.[CH3:31][N:32]([CH3:36])[CH2:33][CH2:34][NH2:35].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:31][N:32]([CH3:36])[CH2:33][CH2:34][NH:35][C:14]([C:12]1[N:13]=[C:8]([C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[C:9]2[S:19][CH:18]=[CH:17][C:10]=2[N:11]=1)=[O:16]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 66053N,N-DimethylethylenediamineHCID 516892Sodium BicarbonateHCID 22674368HCID 22674368, compound

Product 1

HCID 22674414HCID 22674414, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-thienylcarbonyl)thieno[3,2-d]pyrimidine-2-carboxylic acid ( 290 mg, 1.0 mmol) and SOCl2 (4 mL) was refluxed for 30 min, concentrated in vacuo, and treated with CH2Cl2 (10 mL), Et3N (208 μL, 1.5 mmol) and N,N-dimethylethylenediamine (120 μL, 1.1 mmol). The reaction mixture was stirred at room temperature for 1 h, poured into sat. NaHCO3, extracted with EtOAc (2×10 mL), dried (MgSO4), concentrated in vacuo then triturated with EtOAc and filtered to give the title compound (234 mg, 65%) as a cream solid.

Workup

  1. temperaturewas refluxed for 30 min
  2. concentrationconcentrated in vacuo
  3. extractionextracted with EtOAc (2×10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customthen triturated with EtOAc
  7. filtrationfiltered

Sources & evidence

ORD record
ord-4aff654a8e4942f585c68e0f4922ef58
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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