Diisopropylamine → HCID 178494157, compound

HRID 706035Notes

Reaction equation

HRID 706035 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 222931364-(4-Fluorophenoxy)benzylchloride

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-d0a8a9b126614314b136dacf6d02cb84
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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