Dimethylformamide → HCID 136333946, compound

HRID 1022958Notes

Reaction equation

HRID 1022958 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[S:21][C:20]3[C:19](=[O:22])[NH:18][C:17]([CH:23]4[CH2:27][CH2:26][CH2:25][NH:24]4)=[N:16][C:15]=3[CH:14]=2)[C:10]([CH3:28])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(N(C(C)C)C(C)C)C.CN(C)C=O>O.C(OCC)(=O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[S:21][C:20]3[C:19](=[O:22])[NH:18][C:17]([CH:23]4[CH2:27][CH2:26][CH2:25][N:24]4[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[N:16][C:15]=3[CH:14]=2)[C:10]([CH3:28])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 136333941HCID 136333941, compound

Product 1

HCID 136333946HCID 136333946, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-(1-benzyl-3-methyl-1H-pyrazol-4-yl)-2-(pyrrolidin-2-yl)thieno[3,2-d]pyrimidin-4(3H)-one (391 mg) produced in Example 124, step C, ethyl 2-bromoacetate (184 mg), N-ethyl-N-(1-methylethyl)propan-2-amine (258 mg) and N,N-dimethylformamide (5 mL) was stirred at 60° C. for 2 hr. Ethyl acetate (50 mL) and water (50 mL) were added, and the separated aqueous layer was extracted with ethyl acetate (10 mL×2). The combined organic layers were washed with brine (20 mL) and dried over anhydrous magnesium sulfate. Insoluble material was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography (ethyl acetate/hexane) to give the title compound (140 mg) as a colorless solid.

Workup

  1. extractionthe separated aqueous layer was extracted with ethyl acetate (10 mL×2)
  2. washThe combined organic layers were washed with brine (20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customInsoluble material was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by basic silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5c0ef3ff40944cfda4c0fa81fdbe6b41
Source dataset
uspto-grants-2014_05
Patent number
US08722660B2

Reaction notes

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