Dimethylformamide → HCID 12953043, compound

HRID 904580Notes

Reaction equation

HRID 904580 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12](O)=[O:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[CH2:15][S:16][CH2:17][C:3]1=2.C[N:19](C)C=O>O1CCCC1>[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12]([NH2:19])=[O:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[CH2:15][S:16][CH2:17][C:3]1=2

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 12953042HCID 12953042, compound

Product 1

HCID 12953043HCID 12953043, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,10-dihydro-10-oxo-1H-pyrido[1,2-a]thieno[3,4-d]pyrimidine-7-carboxylic acid (4.4 g., 0.018 mol) and 1,1'-carboxyldiimidazole (2.9 g., 0.018 mol) in tetrahydrofuran (300 ml) and dimethylformamide (4 ml) is refluxed under nitrogen for 3.5 hours. The solution is cooled in an ice bath and anhydrous ammonia is bubbled through for 45 minutes. The precipitate is filtered off, washed with hot 0.5 M. aqueous sodium bicarbonate solution, with hot dimethylformamide with ether and dried to give a yellow powder (2.9 g.). mp 285° C. (dec).

Workup

  1. temperatureis refluxed under nitrogen for 3.5 hours
  2. temperatureThe solution is cooled in an ice bath
  3. customanhydrous ammonia is bubbled through for 45 minutes
  4. filtrationThe precipitate is filtered off
  5. washwashed with hot 0.5 M
  6. dry with materialaqueous sodium bicarbonate solution, with hot dimethylformamide with ether and dried
  7. customto give a yellow powder (2.9 g.)

Sources & evidence

ORD record
ord-090454d38a7446af99444f33dd033352
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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