Imidazole → HCID 58169380, compound

HRID 1484860Notes

Reaction equation

HRID 1484860 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[C:5]([CH2:17][OH:18])=[CH:4][N:3]=1.N1C=CN=C1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26].O>C(Cl)Cl>[Si:28]([O:18][CH2:17][C:5]1[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:15][CH2:16]3)[NH:11][N:10]=2)=[N:7][C:2]([Cl:1])=[N:3][CH:4]=1)([C:25]([CH3:27])([CH3:26])[CH3:24])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 58169454HCID 58169454, compound

Product 1

HCID 58169380HCID 58169380, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of (2-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-5-yl)methanol (350 mg, 1.32 mmol), imidazole (107.6 mg, 1.58 mmol, 1.2 eq), TBDMSCl (238 mg, 1.58 mmol, 1.2 eq) in CH2Cl2 (10 mL) was stirred at 20° C. for 16 h. Water (30 mL) was added and the reaction was extracted with CH2Cl2 (4×30 mL). The combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated to afford 5-((tert-butyldimethylsilyloxy)methyl)-2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (500 mg, 99%). LC-MS (m/z)=380.0 [M+H]+.

Workup

  1. extractionthe reaction was extracted with CH2Cl2 (4×30 mL)
  2. washThe combined organic phases were washed (brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9ff8f901855447479c12285546a4f4a8
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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