Diisopropylethylamine → HCID 71251467, compound

HRID 576761Notes

Reaction equation

HRID 576761 reaction equation
[NH2:1][C:2]1[C:3](=[O:22])[N:4]([CH2:20][CH3:21])[C:5](=[O:19])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7]=1[CH3:8].[CH3:23][O:24][CH2:25][CH2:26][C:27](O)=[O:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[CH2:20]([N:4]1[C:3](=[O:22])[C:2]([NH:1][C:27](=[O:28])[CH2:26][CH2:25][O:24][CH3:23])=[C:7]([CH3:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:17])([F:16])[F:18])[CH:10]=2)[C:5]1=[O:19])[CH3:21]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 1344423-Methoxypropionic acidHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71251405HCID 71251405, compound

Product 1

HCID 71251467HCID 71251467, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-amino-3-ethyl-6-methyl-1-(3-trifluoromethylphenyl)pyrimidin-2,4(1H,3H)-dione (prepared in Reference Example 239) (200 mg), 3-methoxypropionic acid (0.15 ml), HATU (487 mg), HOAT (174 mg) and diisopropylethyl amine (0.21 ml) in DMF (5.0 ml) was stirred at room temperature for two hours. To the reaction mixture was added water (10 ml) and the resulting mixture was extracted with ethyl acetate (10 ml×2). The organic layer was washed with water (10 ml) and saturated saline (10 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford the above-mentioned N-(3-ethyl-6-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-3-methoxypropaneamide (222 mg). UPLC/MS 400 (M+H)/0.754 min. (measurement condition 9)

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (10 ml×2)
  2. washThe organic layer was washed with water (10 ml) and saturated saline (10 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0e8c1947e8ca41028273fe0194a2bfe3
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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