Imidazole → 5-(((tert-Butyldimethylsilyl)oxy)methyl)thiazol-2-amine

HRID 1684948Notes

Reaction equation

HRID 1684948 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([NH2:8])=[N:5][CH:4]=1.[CH3:9][C:10]([Si:13](Cl)([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C.CCOCC.O>[Si:13]([O:1][CH2:2][C:3]1[S:7][C:6]([NH2:8])=[N:5][CH:4]=1)([C:10]([CH3:12])([CH3:11])[CH3:9])([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11217273(2-Aminothiazol-5-yl)methanol

Product 1

HCID 575413285-(((tert-Butyldimethylsilyl)oxy)methyl)thiazol-2-amineYield 44.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(hydroxymethyl)-thiazol-2-ylamine (0.787 g, 6.05 mmol), TBDMSCl (1.003 g, 6.65 mmol) and imidazole (0.49 g, 7.26 mmol) in DMF (15 mL) is stirred at room temperature for 24 h. The reaction mixture is diluted with ether and water. The organic layer is washed with water (3×). The aqueous washings are backwashed with ether (2×). The organic layers are combined, dried over MgSO4 and condensed. The crude material is purified using a plug of silica and eluting with 1:1 petrol:ethyl acetate to give the product (0.656 g, 44%). 1H-NMR (400 MHz, d6-DMSO) =0.01 (s, 6H, 2×CH3), 0.82 (s, 9H, tBu), 4.61 (s, 2H, CH2), 4.74 (brs, 2H, NH2), 6.8 (s, 1H, CH). LCMS: Rt 2.62 min (92.7%). MS (MH+, m/z) 245.

Workup

  1. washThe organic layer is washed with water (3×)
  2. dry with materialdried over MgSO4 and condensed
  3. customThe crude material is purified
  4. washeluting with 1:1 petrol

Sources & evidence

ORD record
ord-8db3fd174cdd473293284a4cf0703c98
Source dataset
uspto-grants-2012_04
Patent number
US08148369B2

Reaction notes

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