Imidazole → HCID 89630146, compound

HRID 882172Notes

Reaction equation

HRID 882172 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[C:16]2[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)=[N:14][CH:13]=[N:12][C:11]=2[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:9]=1)=O)(=[O:3])[CH3:2].N1C=CN=C1.C(Br)(Br)(Br)Br.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>ClCCl>[CH3:2][C:1]1[O:3][C:6]([C:8]2[C:16]3[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=4)=[N:14][CH:13]=[N:12][C:11]=3[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:33])[CH3:32])[CH:9]=2)=[N:5][N:4]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 89630032HCID 89630032, compound

Product 1

HCID 89630146HCID 89630146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N′-acetyl-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbohydrazide (470 mg, 1.00 mmol) in dichloromethane (10 mL) was added imidazole (0.15 g, 2.2 mmol), CBr4 (0.72 g, 2.2 mmol) and PPh3 (0.58 g, 2.2 mmol). The reaction was stirred for 1 hour at room temperature and then concentrated in vacuo. The reaction was purified by chromatography using silica gel, eluting with 1-20% ethyl acetate/petroleum ether. The product was collected and concentrated in vacuo to afford 2-methyl-5-(4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-1,3,4-oxadiazole as a white solid. 1NMR (300 MHz, CD3OD) δ 9.08 (s, 1H), 8.45-8.34 (m, 3H), 8.01-7.98 (m, 1H), 7.74-7.53 (m, 1H), 5.87 (s, 2H), 3.74-3.69 (m, 2H), 2.29 (s, 3H), 0.98-0.93 (m, 2H), 0.02 (s, 9H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe reaction was purified by chromatography
  3. washeluting with 1-20% ethyl acetate/petroleum ether
  4. customThe product was collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9c9e4811dad4336bb55b7cc00020dee
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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