1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(6-Amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-benzyloxy-benzamide

HRID 925535Notes

Reaction equation

HRID 925535 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:30])[N:21]([CH2:27][CH2:28][CH3:29])[C:22](=[O:26])[NH:23][C:24]=1[NH2:25].CCN=C=NCCCN(C)C>CO>[NH2:25][C:24]1[NH:23][C:22](=[O:26])[N:21]([CH2:27][CH2:28][CH3:29])[C:20](=[O:30])[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 109542025,6-Diamino-3-propylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 67133662N-(6-Amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-benzyloxy-benzamideYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of 4-benzyloxy-benzoic acid (7.44 g, 0.033 mol), 5,6-diamino-3-propyl-1H-pyrimidine-2,4-dione (5.0 g, 0.027 mol), methanol (60 ml), EDCI (10.0 g, 0.052 mol), were taken and stirred for 20 hours at 20-25° C. The reaction mixture was concentrated and water (50 ml) was added to obtain solid precipitate. The compound was purified by column chromatography to obtain N-(6-Amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-benzyloxy-benzamide as light yellow solid (4.0 g, 38%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater (50 ml) was added
  3. customto obtain solid precipitate
  4. customThe compound was purified by column chromatography

Sources & evidence

ORD record
ord-5a78982cdb48426aa6358726ab230d02
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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