Diisopropylamine → HCID 178494157, compound

HRID 474799Notes

Reaction equation

HRID 474799 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11](=[O:17])[NH:12][C:13](=[S:16])[NH:14][CH:15]=2)=[CH:5][N:4]=1.Cl[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1.C(NC(C)C)(C)C>C(Cl)Cl.CC(=O)OCC>[F:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][C:23]2[CH:24]=[CH:25][C:20]([CH2:19][S:16][C:13]3[NH:14][CH:15]=[C:10]([CH2:9][C:6]4[CH:7]=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=4)[C:11](=[O:17])[N:12]=3)=[CH:21][CH:22]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 219362445-(2-Methoxypyrimidin-5-ylmethyl)-2-thiouracilHCID 22293136HCID 22293136, compound

Product 1

HCID 178494157HCID 178494157, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-((2-methoxypyrimidin-5-yl)methyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (2.75 g, 10.99 mmol), 1-(chloromethyl)-4-(4-fluorophenoxy)benzene (2.6 g, 10.99 mmol) and diisopropylamine (3.34 g, 33.0 mmol) in DCM (50 mL) was heated at 60° C. overnight. After cooling to room temperature, the mixture was washed with brine, the organic phase was dried over Na2SO4, filtered and concentrated to leave the crude product, which was slurred in EA (20 mL) for 10 min, filtered, washed with EA and concentrated in vacuo to afford the title compound (2.75 g, 51.4% yield) as white solid. LCMS: rt=1.47 min, [M+H+]=451.0

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe mixture was washed with brine
  3. dry with materialthe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto leave the crude product, which
  7. filtrationfiltered
  8. washwashed with EA
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1355e430dced4c668b23aa021b194175
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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