Water → HCID 69560031, compound

HRID 1796115Notes

Reaction equation

HRID 1796115 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH3:10][C:11]([C:21]1[CH:26]=[CH:25][N:24]2[C:27]([C:30]3[CH:35]=[CH:34][N:33]=[C:32]([C:36](O)([CH3:38])[CH3:37])[N:31]=3)=[CH:28][N:29]=[C:23]2[N:22]=1)([O:13][Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:12].O.C([O-])(O)=O.[Na+]>ClCCCl>[F:7][C:36]([C:32]1[N:31]=[C:30]([C:27]2[N:24]3[CH:25]=[CH:26][C:21]([C:11]([CH3:12])([O:13][Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:10])=[N:22][C:23]3=[N:29][CH:28]=2)[CH:35]=[CH:34][N:33]=1)([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 69560022HCID 69560022, compound

Product 1

HCID 69560031HCID 69560031, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(Diethylamino)sulphur trifluoride (150 mg, 0.95 mmol) was added to a stirred solution of 2-{4-[7-(1-methyl-1-triethylsilanyloxyethyl)-imidazo[1,2-α]pyrimidin-3-yl]pyrimidin-2-yl}propan-2-ol (Example 115, Step 1) (200 mg, 0.47 mmol) in 1,2-dichloroethane (5 ml) at room temperature under N2 and the reaction was stirred overnight. Water (20 ml) was added followed by NaHCO3 solution (20 ml) and then the organics were extracted with CH2Cl2 (3×50 ml) and concentrated under reduced pressure. The residue was purified by column chromatography on silica using 7% EtOH/EtOAc to yield 3-[2-(1-fluoro-1-methylethyl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine (60 mg, 30%): 1H NMR (400 MHz, CDCl3) δ 10.25 (1H, d, J 7.3), 8.71 (1H, d, J 5.5), 8.48 (1H, s), 7.60 (1H, d, J 7.2), 7.55 (1H, d, J 5.5), 1.87 (6H, d, J 21.6), 0.99 (9H, t, J 8.0), 0.68 (6H, q, J 8.0); m/z (ES+) 430 (M+H+).

Workup

  1. extractionthe organics were extracted with CH2Cl2 (3×50 ml)
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica using 7% EtOH/EtOAc

Sources & evidence

ORD record
ord-0a2a655312534a79a45a5d154daf4e20
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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