Imidazole → 3-(tert-Butyl)-1-(4-(((triisopropylsilyl)oxy)methyl)phenyl)-1H-pyrazol-5-amine

HRID 1427405Notes

Reaction equation

HRID 1427405 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=2)[N:5]=[C:4]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:3]=1.N1C=CN=C1.Cl[Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27]>C1COCC1>[C:15]([C:4]1[CH:3]=[C:2]([NH2:1])[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][O:14][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])=[CH:9][CH:8]=2)[N:5]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 58532567(4-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl)methanol

Product 1

HCID 866877993-(tert-Butyl)-1-(4-(((triisopropylsilyl)oxy)methyl)phenyl)-1H-pyrazol-5-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl)methanol (Ito, K. et al., WO 2010/067131) (8.50 g, 35.0 mmol) and 1H-imidazole (2.71 g, 39.8 mmol) in dry THF (100 mL) under N2 was added chlorotriisopropylsilane (8.16 mL, 38.1 mmol) and the reaction mixture maintained at RT for 5 days. The resulting mixture was evaporated in vacuo and the residue was partitioned between EtOAc (250 mL) and water (100 mL). The organic layer was separated and was washed with (water (100 mL) and brine (80 mL) and then dried and evaporated in vacuo to afford the title compound, Intermediate A12 as a dark red solid (14.6 g, 97%); Rt 3.26 min (Method 2); m/z 402 (M+H)+, (ES+).

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc (250 mL) and water (100 mL)
  3. customThe organic layer was separated
  4. washwas washed with (water (100 mL) and brine (80 mL)
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-03026a035962419d8cfc03f42d457da2
Source dataset
uspto-grants-2015_01
Patent number
US08933228B2

Reaction notes

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