Cesium carbonate → HCID 86679632, compound

HRID 577689Notes

Reaction equation

HRID 577689 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:4]([O:19][C:20]2[CH:21]=[C:22]([NH:26][C:27](=[O:30])[CH:28]=[CH2:29])[CH:23]=[CH:24][CH:25]=2)[N:3]=1.[CH3:31][N:32]1[CH2:36][CH2:35][CH:34]([N:37]2[CH:41]=[C:40]([NH2:42])[CH:39]=[N:38]2)[CH2:33]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:31][N:32]1[CH2:36][CH2:35][CH:34]([N:37]2[CH:41]=[C:40]([NH:42][C:2]3[N:10]=[C:9]4[C:5]([N:6]=[CH:7][N:8]4[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:4]([O:19][C:20]4[CH:21]=[C:22]([NH:26][C:27](=[O:30])[CH:28]=[CH2:29])[CH:23]=[CH:24][CH:25]=4)[N:3]=3)[CH:39]=[N:38]2)[CH2:33]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 679816411-(1-Methyl-3-pyrrolidinyl)-1H-pyrazol-4-amineHCID 86679631N-{3-[(2-chloro-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purin-6-yl)oxy]phenyl}prop-2-enamide

Product 1

HCID 86679632HCID 86679632, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of N-{3-[(2-chloro-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purin-6-yl)oxy]phenyl}prop-2-enamide (210 mg, 0.471 mmol) and 1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-amine (93.9 mg, 0.565 mmol) in 1,4-dioxane (7.85 mL) were added Pd2(dba)3 (43.0 mg, 10 mol %), Xantphos (27.2 mg, 10 mol %), and cesium carbonate (460 mg, 1.41 mmol). The reaction vial was sealed, then evacuated and back-filled with nitrogen three times. The mixture was subjected to microwave irradiation at 140° C. for 1 hr at normal absorption. After cooling to rt the reaction was diluted with EtOAc and filtered through a glass fiber filter set. The filtrate was concentrated and dried to give the title compound, which was carried forward without further purification, assuming quantitative yield. m/z (APCI+) for C28H37N9O3Si 576.20 (M+H)+.

Workup

  1. customThe reaction
  2. customvial was sealed
  3. customevacuated
  4. additionback-filled with nitrogen three times
  5. customirradiation at 140° C. for 1 hr
  6. customat normal absorption
  7. additionwas diluted with EtOAc
  8. filtrationfiltered through a glass fiber
  9. filtrationfilter
  10. concentrationThe filtrate was concentrated
  11. customdried

Sources & evidence

ORD record
ord-36a2c4a4d00744c4916ee0235f1bfb6c
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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