Morpholine → HCID 86706932, compound

HRID 1750252Notes

Reaction equation

HRID 1750252 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])=[CH:24][N:23]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:19]=2[N:20]=[CH:21][N:22]=1>C(O)CCC>[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]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:24]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 867069334-chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 86706932HCID 86706932, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Morpholine (2.45 g, 28.1 mmol) and N,N-diisopropylethylamine (6.63 g, 51.3 mmol) were added to a solution of 4-chloro-5-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (C1) (10.5 g, 25.6 mmol) in n-butanol (300 mL), and the reaction mixture was heated at reflux for 18 hours, then concentrated under reduced pressure. Aqueous hydrochloric acid (0.1 M, 100 mL) was added and the resulting solid was collected by filtration, washed with water (20 mL) and dried under vacuum to provide the product as a yellow solid. Yield: 8.0 g, 17 mmol, 66%. LCMS m/z 461.2 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 8.39 (s, 1H), 7.81 (s, 1H), 5.52 (s, 2H), 3.80-3.86 (m, 4H), 3.46-3.53 (m, 6H), 0.77-0.84 (m, 2H), −0.10 (s, 9H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated under reduced pressure
  4. additionAqueous hydrochloric acid (0.1 M, 100 mL) was added
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with water (20 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-d4a316004da642f5bb84e07558cdac92
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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