Morpholine → 4-{5-[2-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethoxy]-2,6-dichloro-pyrimidin-4-yl}-morpholine

HRID 528491Notes

Reaction equation

HRID 528491 reaction equation
[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][CH:7]([CH:19]1[CH2:21][CH2:20]1)[CH2:8][O:9][C:10]1[C:11](Cl)=[N:12][C:13]([Cl:17])=[N:14][C:15]=1[Cl:16])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[C:1]([Si:5]([CH3:22])([CH3:23])[O:6][CH:7]([CH:19]1[CH2:21][CH2:20]1)[CH2:8][O:9][C:10]1[C:11]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[N:12][C:13]([Cl:17])=[N:14][C:15]=1[Cl:16])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 867117655-[2-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethoxy]-2,4,6-trichloro-pyrimidine

Product 1

HCID 867117664-{5-[2-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethoxy]-2,6-dichloro-pyrimidin-4-yl}-morpholineYield 84%

Procedure

To a solution of 5-[2-(tert-butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethoxy]-2,4,6-trichloro-pyrimidine (411 mg, 1.03 mmol) in IMS (5 mL) was added triethylamine (215 μL, 1.55 mmol) followed by morpholine (94 μL, 1.08 mmol). The reaction mixture was stirred at RT for 4 hours before being concentrated in vacuo. The resultant residue was purified by column chromatography (SiO2, gradient 0-20% ethyl acetate in cyclohexane) to afford 4-{5-[2-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethoxy]-2,6-dichloro-pyrimidin-4-yl}-morpholine as a colorless gum (387 mg, 84%). LCMS: RT=5.22 min, [M+H]+=448/450/452.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customThe resultant residue was purified by column chromatography (SiO2, gradient 0-20% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-1ec93b5dfdba4ccf8b8009705811d99a
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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