Methanol → (NE)-N-[3-[4-[7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-4-yl]pyrazol-1-yl]pentylidene]hydroxylamine

HRID 40962Notes

Reaction equation

HRID 40962 reaction equation
[CH3:1][Si:2]([CH3:28])([CH3:27])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[CH:17]=[N:18][N:19]([CH:21]([CH2:25][CH3:26])[CH2:22][CH2:23]O)[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1.CO.Cl.[NH2:32][OH:33].C(=O)(O)[O-].[K+]>O>[CH3:27][Si:2]([CH3:28])([CH3:1])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[CH:17]=[N:18][N:19]([CH:21]([CH2:25][CH3:26])[CH2:22]/[CH:23]=[N:32]/[OH:33])[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1

Participants

6

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 516893Potassium BicarbonateHCID 57477899HCID 57477899, compound

Product 1

HCID 57477901(NE)-N-[3-[4-[7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-4-yl]pyrazol-1-yl]pentylidene]hydroxylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanal (60 mg, 0.0002 mol) from Example 498, Step 2 in methanol (2 mL, 0.05 mol) was added hydroxylamine hydrochloride (16 mg, 0.00022 mol) and potassium bicarbonate (22 mg, 0.00022 mol). The reaction was stirred at room temperature for 2 h, water was added and the product was extracted with ethyl acetate. The combined extracts were washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give (1E)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanal oxime as a semisolid residue (50 mg, 80%). LC/MS (M+H)+: m/z=415.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe combined extracts were washed with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1508a01c11e84f3e82ac4c40ac435a9d
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Reaction notes

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