Ethyl Acetate → HCID 66699756, compound

HRID 388143Notes

Reaction equation

HRID 388143 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][N:9]2[C:13]3=[N:14][C:15]([Sn](C)(C)C)=[CH:16][N:17]=[C:12]3[NH:11][C:10]2=[O:22])[CH2:3][CH2:2]1.BrC1N=C2[N:30]([CH2:34][CH2:35][CH:36]3[CH2:41][CH2:40]OCC3)[C:31](=[O:33])NC2=NC=1.C[Sn](C)C.C[Sn](C)C.O1CCO[CH2:52][CH2:51]1.[C:56](OCC)(=O)[CH3:57]>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>[O:33]=[C:31]1[NH:30][CH:34]([C:35]2[CH:36]=[CH:41][C:40]([C:15]3[N:14]=[C:13]4[N:9]([CH2:8][CH2:7][CH:4]5[CH2:5][CH2:6][O:1][CH2:2][CH2:3]5)[C:10](=[O:22])[NH:11][C:12]4=[N:17][CH:16]=3)=[CH:52][CH:51]=2)[CH2:57][CH2:56]1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 6327618HexamethylditinHCID 66699960HCID 66699960, compoundHCID 86626416HCID 86626416, compound

Product 1

HCID 66699756HCID 66699756, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

1-(2-(Tetrahydro-2H-pyran-4-yl)ethyl)-6-(trimethylstannyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. 6-Bromo-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (1.00 g, 3.06 mmol), hexamethylditin (1.20 g, 3.67 mmol), tetrakis(triphenylphosphine)palladium(0) (0.71 g, 0.61 mmol), and 1,4-dioxane (10 mL) were combined in a 150 mL sealable vessel with a stirbar. Nitrogen was blown into the vessel to blow out air and the vessel was sealed. The resulting reaction mixture was stirred vigorously and heated at 100° C. for 5 h and then cooled to room temperature. The resulting mixture was diluted with ethyl acetate and filtered through Celite. The filter cake was washed thoroughly with ethyl acetate. The filtrate was concentrated on a rotary evaporator. Flash chromatography (30-60% ethyl acetate in hexane) gave the desired product (783 mg, 62%) as a yellow waxy solid. Rf=0.20 (50% ethyl acetate/hexane); 1H NMR (400 MHz, DMSO-d6) δ 11.84 (s, 1H), 7.88 (s, 1H), 3.87 (t, J=6.64, 2H), 3.80 (dd, J=11.32, 3.12, 2H), 3.18 (t, J=10.93, 2H), 1.60-1.73 (m, 4H), 1.33-1.46 (m, 1H), 1.08-1.23 (m, 2H), 0.31 (s, 9H); MS (ESI) m/z 413[M+1]+.

Workup

  1. customthe vessel was sealed
  2. customThe resulting reaction mixture
  3. temperaturecooled to room temperature
  4. filtrationfiltered through Celite
  5. washThe filter cake was washed thoroughly with ethyl acetate
  6. concentrationThe filtrate was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-d1e29d4e02c448e6a691b4c9a1f5c094
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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