HCID 67430540, compound → Tert-butyl 4-{[2-({3-amino-5-[2-(1-hydroxycyclobutyl)-1,3-thiazol-5-yl]phenyl}amino)pyrimidin-4-yl]-oxy}piperidine-1-carboxylate

HRID 410643Notes

Reaction equation

HRID 410643 reaction equation
[OH:1][C:2]1([C:6]2[S:7][C:8]([C:11]3[CH:12]=[C:13]([NH:20][C:21]4[N:26]=[C:25]([O:27][CH:28]5[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]5)[CH:24]=[CH:23][N:22]=4)[CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=3)=[CH:9][N:10]=2)[CH2:5][CH2:4][CH2:3]1>CO.[Pt]>[NH2:17][C:15]1[CH:14]=[C:13]([NH:20][C:21]2[N:26]=[C:25]([O:27][CH:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32][CH2:33]3)[CH:24]=[CH:23][N:22]=2)[CH:12]=[C:11]([C:8]2[S:7][C:6]([C:2]3([OH:1])[CH2:5][CH2:4][CH2:3]3)=[N:10][CH:9]=2)[CH:16]=1

Participants

4

Reactant 1

HCID 67430540HCID 67430540, compound

Product 1

HCID 67430891Tert-butyl 4-{[2-({3-amino-5-[2-(1-hydroxycyclobutyl)-1,3-thiazol-5-yl]phenyl}amino)pyrimidin-4-yl]-oxy}piperidine-1-carboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To the product from Step 2 (320 mg, 0.563 mmol) in MeOH (2.8 mL) was added Pt/C doped with V (3% wt, 110 mg, 0.017 mmol) and the mixture was stirred under H2 balloon for 2 h. The mixture was passed through a silica gel pack and washed with DCM/MeOH. Solvent was removed in vacuo and the residue was purified using column chromatography on silica gel (0-100%, ethyl acetate: 10:1 methanol in DCM) to afford 250 mg (0.46 mmol, 82%) of tert-butyl 4-{[2-({3-amino-5-[2-(1-hydroxycyclobutyl)-1,3-thiazol-5-yl]phenyl}amino)pyrimidin-4-yl]-oxy}piperidine-1-carboxylate as yellow solid. MS ESI: [M+H]+ m/z 539.3.

Workup

  1. washwashed with DCM/MeOH
  2. customSolvent was removed in vacuo
  3. customthe residue was purified

Sources & evidence

ORD record
ord-55a01aaab31e41a9a67e455aaa47abb2
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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