Imidazole → 6-[2-(Tert-butyl-dimethyl-silanyloxy)-2-methyl-propoxy]-2-morpholin-4-yl-pyrimidin-4-ylamine

HRID 641179Notes

Reaction equation

HRID 641179 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([O:14][CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[CH:3]=1.N1C=CN=C1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].C(OCC)(=O)C>CN(C)C=O>[C:28]([Si:25]([CH3:27])([CH3:26])[O:18][C:16]([CH3:19])([CH3:17])[CH2:15][O:14][C:4]1[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:7]=[C:2]([NH2:1])[CH:3]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 68517032HCID 68517032, compound

Product 1

HCID 685174336-[2-(Tert-butyl-dimethyl-silanyloxy)-2-methyl-propoxy]-2-morpholin-4-yl-pyrimidin-4-ylamineYield 34.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(6-amino-2-morpholin-4-yl-pyrimidin-4-yloxy)-2-methyl-propan-2-ol (1.03 g; 3.8 mmol) and imidazole (500 mg; 8 mmol) were-dissolved in dimethyl formamide (16 mL). To this solution was added tert-butyldimethylsilyl chloride (1.2 g; 8 mmol), and it was stirred for 72 hours. The solution was poured into ethyl acetate (100 mL) which was then washed with water (3×200 mL). The organic layer was separated, dried over magnesium sulfate, and purified by column chromatography to give 6-[2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propoxy]-2-morpholin-4-yl-pyrimidin-4-ylamine (500 mg).

Workup

  1. washwas then washed with water (3×200 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-6de1d9f9ff77495bb754b91dc9f263a8
Source dataset
uspto-grants-2010_04
Patent number
US07696202B2

Reaction notes

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