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Stannane, tributyl-(1Z)-1-propen-1-yl- → HCID 50943072, compound

HRID 1484843
Notes
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Reaction equation

HRID 1484843 reaction equation
Br[C:2]1[C:3]([NH:14][C:15]2[CH:19]=[C:18]([CH:20]3[CH2:22][CH2:21]3)[NH:17][N:16]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH2:23]([Sn](CCCC)(CCCC)/C=C/C)[CH2:24][CH2:25]C>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH:20]1([C:18]2[NH:17][N:16]=[C:15]([NH:14][C:3]3[C:2](/[CH:23]=[CH:24]/[CH3:25])=[CH:7][N:6]=[C:5]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:4]=3)[CH:19]=2)[CH2:22][CH2:21]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 5315049Stannane, tributyl-(1Z)-1-propen-1-yl-HCID 50943139HCID 50943139, compound

Product 1

HCID 50943072HCID 50943072, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418476HCID 178418476, compoundCatalyst
HCID 31275
1,4-Dioxane
Solvent

Procedure

The mixture of 5-bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenylpyrimidin-4-amine (0.3 g, 0.84 mmol, 1.0 equiv.), (E)-tributyl(prop-1-enyl)stannane (0.5 g, 1.5 mmol, 1.5 eq), Bu4NBr (0.32 g, 0.84 mmol, 1.0 eq), Pd(PPh3)2Cl2 (0.1 g, 0.034 mmol, 0.04 eq) and dioxane (10 mL) was heated to reflux for 18 h. Then, silica gel was added to the reaction mixture and evaporated to dry. The residue was purified by silica gel chromatography (hexane/EtOAc/Et3N=100:100:1 as eluent) to generate (E)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenyl-5-(prop-1-enyl)pyrimidin-4-amine (Compound 11) (0.1 g, 37.5%). LC-MS (m/z): 357.2 [M+H]+. 1H NMR (300 MHz, DMSO-d6): δ 0.71-0.72 (m, 2H), 0.94-1.02 (m, 2H), 1.74-1.80 (m, 3H), 1.87-1.96 (m, 1H), 5.98 (d, J=11.4 Hz, 1H), 6.48 (d, J=11.4 Hz, 1H), 7.47-7.49 (m, 3H), 8.24-8.32 (m, 2H), 8.71 (s, 1H), 12.12 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. additionThen, silica gel was added to the reaction mixture
  4. customevaporated
  5. customto dry
  6. customThe residue was purified by silica gel chromatography (hexane/EtOAc/Et3N=100:100:1 as eluent)

Sources & evidence

ORD record
ord-5f142d9240234f08b777d75130592fa0
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422271B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes