Hydrochloric Acid → HCID 67977664, compound

HRID 1468774Notes

Reaction equation

HRID 1468774 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1.C(N(CC)CC)C.Cl[C:30]([O:32][CH3:33])=[O:31].Cl>ClCCl>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:30]([O:32][CH3:33])=[O:31])[CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 67977685HCID 67977685, compound

Product 1

HCID 67977664HCID 67977664, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methyl-2-(piperidine-3-yloxy)-1H-[4,4′]bipyrimidinyl-6-one (0.10 g, 0.35 mmol) and triethylamine (70 μl, 0.5 mmol) in dichloromethane (5 ml) was added methyl chloroformate (40 μl, 0.5 mmol) at 0° C. The resulting mixture was stirred for 2 hours and poured into 1N aqueous hydrochloric acid. The partitioned organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent; chloroform/methanol=100/0 to 90/10) to afford methyl 3-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yloxy)piperidine-1-carboxylate as a white solid (52 mg, 0.15 mmol, 43%).

Workup

  1. dry with materialThe partitioned organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (eluent; chloroform/methanol=100/0 to 90/10)

Sources & evidence

ORD record
ord-8915872d72da4f139a70d7eb489a3168
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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