1,1'-Carbonyldiimidazole → HCID 59300334, compound

HRID 2236448Notes

Reaction equation

HRID 2236448 reaction equation
[C:1]([CH2:4][C:5]1[C:10]([C:11](O)=[O:12])=[CH:9][N:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1)(=[O:3])[NH2:2].C1N=CN(C(N2C=NC=C2)=O)C=1>CN(C)C=O>[C:14]1([C:7]2[N:8]=[CH:9][C:10]3[C:11](=[O:12])[NH:2][C:1](=[O:3])[CH2:4][C:5]=3[N:6]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59299831HCID 59299831, compound

Product 1

HCID 59300334HCID 59300334, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.670 g (2.61 mmol) of 4-Carbamoylmethyl-2-phenyl-pyrimidine-5-carboxylic Acid and 0.528 g (3.26 mmol) of CDI in 20 mL of N,N-dimethylformamide is stirred overnight at 25° C. The solvent is evaporated and the residue is washed with Et2O (3×). The insoluble material is boiled with CHCl3, collected, washed with hot CHCl3 and Et2O and dried in vacuo to give 0.372 g (60%) of yellow-orange crystals: mp 216-217.5° C. (dec); 1H NMR (DMSO-d6) δ 8.99 (s, 1H), 8.41 (m, 2H), 7.56 (m, 4H), 5.45 (s, 2H); HRMS (ESI) m/e calcd for C13H9N3O2 240.07645. found 240.07652 (M+H)+1. Analysis for C13H9N3O2.0.25H2O: Calcd: C, 64.05; H, 3.94; N, 17.24. Found: C, 63.67; H, 3.91; N, 17.38.

Workup

  1. customThe solvent is evaporated
  2. washthe residue is washed with Et2O (3×)
  3. customcollected
  4. washwashed with hot CHCl3 and Et2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b5e01f0ca4f543a2bcbb2c8d203c45a4
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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