Methanol → HCID 70896477, compound

HRID 1397045Notes

Reaction equation

HRID 1397045 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:21]=[C:20](Cl)[N:19]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[CH:17]=2)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>[Pd].CCN(CC)CC>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:21]=[CH:20][N:19]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[CH:17]=2)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 86672859HCID 86672859, compound

Product 1

HCID 70896477HCID 70896477, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A 50 mL round-bottomed flask was charged with methyl 6-(4-(((tert-butoxycarbonyl)amino)methyl)piperidin-1-yl)-2-chloropyrimidine-4-carboxylate and MeOH (4 mL) and Et3N (0.4 mL). 10% Pd/C (104 mg, 0.25 equiv.) was added under argon. The reaction mixture was stirred for 6 h under 1 atm H2. The catalyst was filtered and the solvent was evaporated to give the crude desired product (150 mg, 110% crude yield) which was used directly in the next step. LC-MS m/z 351 (M+1).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-36888eb3853648f2bf411f700d17fa5d
Source dataset
uspto-grants-2014_12
Patent number
US08901145B2

Reaction notes

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