Allyl Alcohol → HCID 89630017, compound

HRID 882117Notes

Reaction equation

HRID 882117 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([C:11]3[C:12]4[C:19]([C:20]([OH:22])=[O:21])=[CH:18][N:17]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:13]=4[N:14]=[CH:15][N:16]=3)[CH:7]=[CH:8]2)=[N:3]1.CN(C(ON1N=N[C:41]2[CH:42]=CC=N[C:40]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(O)C=C.CCN(C(C)C)C(C)C>CS(C)=O>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([C:11]3[C:12]4[C:19]([C:20]([O:22][CH2:42][CH:41]=[CH2:40])=[O:21])=[CH:18][N:17]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:13]=4[N:14]=[CH:15][N:16]=3)[CH:7]=[CH:8]2)=[N:3]1

Participants

6

Reactant 4

HCID 7858Allyl Alcohol2×HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 89629949HCID 89629949, compound

Product 1

HCID 89630017HCID 89630017, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-(2-Methyl-2H-indazol-6-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (50 mg, 0.12 mmol), HATU (90 mg, 0.24 mmol), and allyl alcohol (0.016 mL, 0.24 mmol) were sequentially added to DMSO (1.0 mL) followed by the addition of Hunig's base (0.10 mL, 0.59 mmol). The reaction was stirred for 17 hours at room temperature at which point an additional amount of HATU (90 mg, 0.24 mmol), Hunig's base (0.10 mL, 0.59 mmol) and allyl alcohol (0.016 mL, 0.24 mmol) were added. The reaction was stirred at room temperature for 17 hours and then extracted with EtOAc (×3) from a saturated sodium bicarbonate solution. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give prop-2-en-1-yl 4-(2-methyl-2H-indazol-6-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calcd for C24H30N5O3Si [M+H]+: 464, found 464.

Workup

  1. additionwere added
  2. extractionextracted with EtOAc (×3) from a saturated sodium bicarbonate solution
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c741d087fd034be0a76e923f89681e06
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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