Morpholine → HCID 86706965, compound

HRID 1750295Notes

Reaction equation

HRID 1750295 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.Cl[C:17]1[C:18]2[C:25]([I:26])=[C:24]([CH:27]=[O:28])[N:23]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:19]=2[N:20]=[CH:21][N:22]=1>C(#N)C>[I:26][C:25]1[C:18]2[C:17]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[N:22][CH:21]=[N:20][C:19]=2[N:23]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:35])[CH3:36])[C:24]=1[CH:27]=[O:28]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 86706964HCID 86706964, compound

Product 1

HCID 86706965HCID 86706965, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Morpholine (1.09 g, 12.5 mmol) and N,N-diisopropylethylamine (2.94 g, 22.7 mmol) were added to a solution of 4-chloro-5-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde (C28) (5.0 g, 11 mmol) in acetonitrile (20 mL). The reaction mixture was stirred at reflux for 16 hours, whereupon it was cooled and concentrated in vacuo; the residue was purified by chromatography on silica gel (Gradient: 0% to 20% ethyl acetate in petroleum ether) to provide the product as a yellow oil. Yield: 4.0 g, 8.2 mmol, 74%. 1H NMR (400 MHz, CDCl3) δ 9.99 (s, 1H), 8.54 (s, 1H), 6.01 (s, 2H), 3.92-3.98 (m, 4H), 3.70-3.75 (m, 4H), 3.58-3.65 (m, 2H), 0.91-0.96 (m, 2H), −0.05 (s, 9H).

Workup

  1. temperatureat reflux for 16 hours, whereupon it
  2. temperaturewas cooled
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by chromatography on silica gel (Gradient: 0% to 20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-377e2e0349e841eb8b0222236959210e
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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