1,1'-Carbonyldiimidazole → HCID 12953069, compound

HRID 1577415Notes

Reaction equation

HRID 1577415 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=[CH:15][S:16][CH:17]=[C:3]12.C(N1C=CN=C1)([N:20]1C=CN=C1)=O>CN(C)C=O>[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12]([NH2:20])=[O:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2=[CH:15][S:16][CH:17]=[C:3]12

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 12953067HCID 12953067, compound

Product 1

HCID 12953069HCID 12953069, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 10-oxo-10H-pyrido[1,2-a]thieno[3,4-d]pyrimidine-7-carboxylic acid (6.0 g., 0.024 mol) and 1,1'-carbonyldiimidazole (4.0 g., 0.024 mol) in dimethylformamide (120 ml) is heated at 110° C. for 2.5 hours under nitrogen. The solution is cooled in an ice bath and anhydrous ammonia is bubbled through for 15 minutes. The mixture is stirred at ice bath temperature for 2 hours and at room temperature for one hour. The precipitate is filtered off, washed with tetrahydrofuran and dried to give the product (5.2 g.), mp 340° C. (dec).

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. customanhydrous ammonia is bubbled through for 15 minutes
  3. waitat room temperature for one hour
  4. filtrationThe precipitate is filtered off
  5. washwashed with tetrahydrofuran
  6. customdried
  7. customto give the product (5.2 g.), mp 340° C. (dec)

Sources & evidence

ORD record
ord-0ed7547efd3548ee808bff608ac70558
Source dataset
uspto-grants-1981_09
Patent number
US04287340

Reaction notes

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