Ethanol → HCID 90402822, compound

HRID 2200615Notes

Reaction equation

HRID 2200615 reaction equation
[NH2:1][C:2]1[C:3](=[O:20])[N:4]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:5](=[O:10])[N:6]([CH3:9])[C:7]=1[NH2:8].[F:21][C:22]([F:37])([F:36])[O:23][C:24]1[CH:25]=[C:26]([CH:33]=[CH:34][CH:35]=1)[O:27][CH2:28][CH2:29][C:30](O)=O.CCN=C=NCCCN(C)C.[CH2:49]([OH:51])C>O>[NH2:8][C:7]1[N:6]([CH3:9])[C:5](=[O:10])[N:4]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:3](=[O:20])[C:2]=1[NH:1][C:49](=[O:51])[CH2:30][CH2:29][CH2:28][O:27][C:26]1[CH:33]=[CH:34][CH:35]=[C:24]([O:23][C:22]([F:37])([F:36])[F:21])[CH:25]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 90402721HCID 90402721, compoundHCID 90402811HCID 90402811, compound2×

Product 1

HCID 90402822HCID 90402822, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5,6-diamino-3-(4-methoxybenzyl)-1-methylpyrimidine-2,4(1H,3H)-dione (100 mg, 0.362 mmol, Intermediate 59) in ethanol (3 mL) was added 3-(3-(trifluoromethoxy)phenoxy)propanoic acid (96 mg, 0.364 mmol) and EDCI (105 mg, 0.546 mmol). The reaction was stirred at room temperature for 3 h. Then the mixture was diluted with water and the precipitate was collected by filtration and rinsed with water. The solids were then dissolved in ethyl acetate. This organic solution was dried over sodium sulfate and concentrated to give N-(6-amino-3-(4-methoxybenzyl)-1-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-4-(3-(trifluoromethoxy)phenoxy)butanamide (150 mg, 79.3%) as a yellow solid. LCMS retention time 1.422 min; LCMS MH+ 523.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washrinsed with water
  3. dissolutionThe solids were then dissolved in ethyl acetate
  4. dry with materialThis organic solution was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a79f458163b548bcae81aca1d009b45c
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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