1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66894144, compound

HRID 889007Notes

Reaction equation

HRID 889007 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][C:19]1[C:20](=[O:33])[N:21]([CH2:30][CH2:31][CH3:32])[C:22](=[O:29])[N:23]([CH2:26][CH2:27][CH3:28])[C:24]=1[NH2:25].CCN=C=NCCCN(C)C>CO>[NH2:25][C:24]1[N:23]([CH2:26][CH2:27][CH3:28])[C:22](=[O:29])[N:21]([CH2:30][CH2:31][CH3:32])[C:20](=[O:33])[C:19]=1[NH:18][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 738804-(Benzyloxy)benzoic acidHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 66894144HCID 66894144, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-benzyloxy-benzoic acid (0.868 g, 3.8 mmol), 5,6-diamino-1,3-dipropyl-1H-pyrimidine-2,4-dione (1.0 g, 3.8 mmol), methanol (15 ml), EDCI (0.95 g, 4.9 mmol), was stirred for 20 hours at room temperature. The reaction mixture was concentrated and water was added to obtain the intermediate N-(6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-benzyloxy-benzamide. It was dissolved in methanol (32 ml) and added 10% NaOH (24 ml). The mixture was heated at 80-90° C. for 3 hours. The mixture was cooled and solvent was removed. The residue was dissolved in water (20 ml) acidified with dil HCl to provide 8-(4-benzyloxy-phenyl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (1.2 g, 75%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added

Sources & evidence

ORD record
ord-a1751f096613485ebc04dd4279ca99d0
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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