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3-Cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amine → 3-Cyclobutyl-1-[1-(2-trimethylsilylethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]imidazo[1,5-a]pyrazin-8-amine

HRID 643402
Notes
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Reaction equation

HRID 643402 reaction equation
[CH3:1][Si:2]([CH3:30])([CH3:29])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[CH:9]=[C:8]1[Sn](CCCC)(CCCC)CCCC.[CH:31]1([C:35]2[N:39]3[CH:40]=[CH:41][N:42]=[C:43]([NH2:44])[C:38]3=[C:37](I)[N:36]=2)[CH2:34][CH2:33][CH2:32]1>C(O)C.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>[CH:31]1([C:35]2[N:39]3[CH:40]=[CH:41][N:42]=[C:43]([NH2:44])[C:38]3=[C:37]([C:8]3[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:29])[CH3:30])[C:11]4=[N:12][CH:13]=[CH:14][CH:15]=[C:10]4[CH:9]=3)[N:36]=2)[CH2:32][CH2:33][CH2:34]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 426093653-Cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amineHCID 59133036N-(2-Trimethylsilyl-1-ethoxymethyl)-2-(tributylstannyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 591330243-Cyclobutyl-1-[1-(2-trimethylsilylethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]imidazo[1,5-a]pyrazin-8-amineYield 24.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compound
Catalyst
HCID 702EthanolSolvent

Procedure

A mixture of N-(2-trimethylsilyl-1-ethoxymethyl)-2-(tributylstannyl)-1H-pyrrolo[2,3-b]pyridine (110 mg, 0.20 mmol), 3-cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amine (50 mg, 0.1592 mmol) and bis(triphenylphosphine)palladium(II) chloride (10 mg, 0.02 mmol) in ethanol (2 mL) was heated at reflux for 48 h. The mixture was then cooled to rt, filtered through a pad of Celite and concentrated in vacuo. The residue thus obtained was chromatographed over silica gel eluting with hex:EtOAc to afford 17.2 mg of the title compound. 1H NMR (400 MHz CDCl3) δ 0.22 (s, 9H), 0.70 (t, 2H), 1.87-2.19 (m, 2H), 2.49-2.64 (m, 4H), 3.37 (t, 2H), 3.81-3.86 (m, 1H), 5.51 (bs, 2H), 6.07 (s, 2H), 6.67 (s, 1H), 7.10-7.16 (m, 3H), 7.93 (dd, J=1.6, 8.0 Hz, 1H) and 8.41 (dd, J=1.6, 4.8 Hz, 1H). MS (ES+): m/z: 435.21 [MH+].

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 h
  3. filtrationfiltered through a pad of Celite
  4. concentrationconcentrated in vacuo
  5. customThe residue thus obtained
  6. customwas chromatographed over silica gel eluting with hex

Sources & evidence

ORD record
ord-19485a909fa24e6d98456d4498a0b06a
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07700594B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes