Tetramethyltin → 4-(2-Methoxyethoxy)-2-(6-methylpyridin-3-yl)-6-(pyrazolo[1,5-a]pyridin-3-ylcarbonyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 452584Notes

Reaction equation

HRID 452584 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([O:29][CH2:30][CH2:31][O:32][CH3:33])[C:11]3[CH2:17][N:16]([C:18]([C:20]4[CH:21]=[N:22][N:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=45)=[O:19])[CH2:15][CH2:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[CH3:34][Sn](C)(C)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:33][O:32][CH2:31][CH2:30][O:29][C:10]1[C:11]2[CH2:17][N:16]([C:18]([C:20]3[CH:21]=[N:22][N:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=34)=[O:19])[CH2:15][CH2:14][C:12]=2[N:13]=[C:8]([C:5]2[CH:6]=[N:7][C:2]([CH3:34])=[CH:3][CH:4]=2)[N:9]=1

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 49821989[2-(6-Chloropyridin-3-yl)-4-(2-methoxyethoxy)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5h)-yl](pyrazolo[1,5-a]pyridin-3-yl)methanone

Product 1

HCID 498220734-(2-Methoxyethoxy)-2-(6-methylpyridin-3-yl)-6-(pyrazolo[1,5-a]pyridin-3-ylcarbonyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidineYield 49%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 30 mg (0.065 mmol) O-2 in 1 mL DMF in a microwave vial was added approximately 20 uL (˜0.15 mmol) tetramethyltin and 8 mg (˜10 mol %) tetrakistriphenylphosphinepalladium(0). The reaction was heated by microwave irradiation for 20 minutes at 150° C. After cooling, the reaction was purified by reverse phase HPLC (CH3CN/H2O with TFA as modifier), and the fractions containing the product were partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to provide R-1 as a white solid (14 mg, 49% yield). HRMS m/z (M+H) 445.1977 found, 445.1983 required.

Workup

  1. temperatureAfter cooling
  2. customthe reaction was purified by reverse phase HPLC (CH3CN/H2O with TFA as modifier)
  3. additionthe fractions containing the product
  4. customwere partitioned between EtOAc and saturated aqueous NaHCO3
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f67e3aa8cdcc486596c9da51813412aa
Source dataset
uspto-grants-2013_07
Patent number
US08492392B2

Reaction notes

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