Dicyclohexylcarbodiimide → 3-[[[4,5-Bis(phenylmethoxy)-2-pyridinyl]carbonyl]amino]-tetrahydro-2-oxo-1(2H)-pyrimidinecarboxamide

HRID 2351091Notes

Reaction equation

HRID 2351091 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([NH2:10])=[O:9])[C:3]1=[O:11].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[C:37]1([CH2:43][O:44][C:45]2[C:50]([O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[CH:49][N:48]=[C:47]([C:59](O)=[O:60])[CH:46]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C)C=O>[C:37]1([CH2:43][O:44][C:45]2[C:50]([O:51][CH2:52][C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)=[CH:49][N:48]=[C:47]([C:59]([NH:1][N:2]3[CH2:7][CH2:6][CH2:5][N:4]([C:8]([NH2:10])=[O:9])[C:3]3=[O:11])=[O:60])[CH:46]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 141825074,5-bis(phenylmethoxy)-2-Pyridinecarboxylic acidHCID 198480103-Amino-2-oxotetrahydropyrimidine-1(2H)-carboxamide

Product 1

HCID 198480113-[[[4,5-Bis(phenylmethoxy)-2-pyridinyl]carbonyl]amino]-tetrahydro-2-oxo-1(2H)-pyrimidinecarboxamideYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-aminotetrahydro-2-oxo-1(2H)-pyrimidinecarboxamide (10 g, 63.2 mmol) in 350 ml N,N-dimethylformamide were added dicyclohexylcarbodiimide (15.7 g, 75.9 mmol), N-hydroxybenzotriazole (0.97 g, 6.32 mmol) and 4,5-bis(phenylmethoxy)-2-pyridinecarboxylic acid (21.2 g, 63.2 mmol) and the mixture was stirred overnight at room temperature. Dicyclohexylurea (13.6 g) was filtered off and the solvent was removed in vacuo. Trituration of the residue with ether gave 27.5 g of the desired product, melting point 192°-195° C.

Workup

  1. filtrationDicyclohexylurea (13.6 g) was filtered off
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4b422f76e06d495ca7961a7988887f21
Source dataset
uspto-grants-1989_10
Patent number
US04871841

Reaction notes

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