Water → HCID 178484864, compound

HRID 577712Notes

Reaction equation

HRID 577712 reaction equation
[CH3:1][N:2]([C@H:10]1[CH2:13][C@H:12]([O:14][C:15]2[C:16]3[C:30]([C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)=[CH:29][N:28](COCC[Si](C)(C)C)[C:17]=3[N:18]=[C:19]([NH:21][C:22]3[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=3)[N:20]=2)[CH2:11]1)C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O.O.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CO>[CH3:1][NH:2][C@H:10]1[CH2:13][C@H:12]([O:14][C:15]2[C:16]3[C:30]([C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)=[CH:29][NH:28][C:17]=3[N:18]=[C:19]([NH:21][C:22]3[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=3)[N:20]=2)[CH2:11]1

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 178480800HCID 178480800, compound

Product 1

HCID 178484864HCID 178484864, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl methyl{trans-3-[(2-[(1-methyl-1H-pyrazol-4-yl)amino]-5-(pyridin-3-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]cyclobutyl}carbamate (250 mg, 0.4 mmol) in DCM (10 mL) was added TFA (0.33 mL). The reaction solution was stirred at ambient temperature for 20 hrs. The volatiles were removed in vacuo to give a residue, which was dissolved in methanol (8 mL). Water (4 mL) and solid K2CO3 (223 mg) were added, and the mixture was stirred at ambient temperature for 2 hrs. The volatiles were then removed in vacuo to give the title compound that was used as crude in the next step.

Workup

  1. customThe volatiles were removed in vacuo
  2. customto give a residue, which
  3. stirringthe mixture was stirred at ambient temperature for 2 hrs
  4. customThe volatiles were then removed in vacuo

Sources & evidence

ORD record
ord-ab327bf34e3544e1a52b26ea05fa2d2a
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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