Hydrochloric Acid → 1-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4']bipyrimidinyl-6-one

HRID 1045692Notes

Reaction equation

HRID 1045692 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([CH3:27])[C:16](=[O:26])[CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][N:21]=3)[N:19]=2)[C@H:10]([CH3:28])[CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[CH3:27][N:15]1[C:16](=[O:26])[CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][N:21]=2)[N:19]=[C:14]1[N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[CH3:28]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57870141(3R)-3-methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 250045961-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4']bipyrimidinyl-6-oneYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (3R)-3-methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (6.9 g, 18 mmol) in ethyl acetate (35 ml) was added hydrogen chloride (4N) in ethyl acetate (35 ml) at room temperature. The mixture was stirred at room temperature for 2 hours and was concentrated under reduced pressure. The residue was partitioned between aqueous sodium hydrogen carbonate and chloroform, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford 1-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4′]bipyrimidinyl-6-one (4.6 g, 91%).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between aqueous sodium hydrogen carbonate and chloroform
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-eb473c79e5984026af4910fb632d4ed7
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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