Dicyclohexylcarbodiimide → HCID 9825688, compound

HRID 399422Notes

Reaction equation

HRID 399422 reaction equation
[NH2:1][C:2]1[C:3](=[O:17])[N:4]([CH3:16])[C:5](=[O:15])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]=1[NH2:8].[OH:18][C:19]1[C:20]([CH3:35])=[C:21]2[C:26](=[C:27]([CH3:30])[C:28]=1[CH3:29])[O:25][C:24]([CH3:34])([C:31](O)=[O:32])[CH2:23][CH2:22]2.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[NH2:8][C:7]1[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:15])[N:4]([CH3:16])[C:3](=[O:17])[C:2]=1[NH:1][C:31]([C:24]1([CH3:34])[CH2:23][CH2:22][C:21]2[C:26](=[C:27]([CH3:30])[C:28]([CH3:29])=[C:19]([OH:18])[C:20]=2[CH3:35])[O:25]1)=[O:32]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 40634TroloxHCID 110752755,6-Diamino-3-methyl-1-phenyluracil

Product 1

HCID 9825688HCID 9825688, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5,6-diamino-3-methyl-1-phenyl-2,4 (1H, 3H) -pyrimidinedione (3.02 g, 13 mmol), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (3.58 g, 14.3 mmol) and 4-(dimethylamino)pyridine (0.32 g, 2.6 mmol) was suspended in dichloromethane (60 mL). To the resultant suspension was added dropwise a solution of N, N'-dicyclohexylcarbodiimide (2.82 g, 13.7 mmol) indichloromethane (60 mL) at room temperature. The reaction mixture was stirred overnight and then filtered. The filtrate was concentrated and then subjected to silica-gel column chromatography, thereby giving the title compound (yield 57%). TOF-MS (Time-of-flight type mass spectrum): m/z 465 [M+H]+1H-NMR (CDC13):δ1.60(3H, s), 1.90-2.04(1H, m), 2.08(3H, s), 2.18(3H, s), 2.29(3H, s), 2.30-2.38(1H, m), 2.54-2.64(2H, m), 3.34(3H, s), 4.32(1H, s), 5.17(2H, bs), 7.27-7.36(2H, m), 7.53-7.60 (3H, m), 8.41 (1H, bs)

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a92ac93861ff4bb688773cf5d7d79206
Source dataset
uspto-grants-1998_10
Patent number
US05821247

Reaction notes

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