Acetic Acid → HCID 11516307, compound

HRID 733162Notes

Reaction equation

HRID 733162 reaction equation
C([BH3-])#N.[NH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C(O)(=O)C.O=[CH:15][CH2:16][CH2:17][C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[N:21]=[C:20]([C:34]#[N:35])[N:19]=1>C(#N)C>[N:4]1([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[N:21]=[C:20]([C:34]#[N:35])[N:19]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 498716Cyano-borohydrideHCID 86619632HCID 86619632, compound

Product 1

HCID 11516307HCID 11516307, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
150 °C

Procedure

To a suspension of macroporous cyanoborohydride (102 mg, 2.35 mmol/g) in acetonitrile (0.5 mL), was added piperidine (19 μL), acetic acid (0.1 mL), and a solution of 4-(3-oxo-propyl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile (49 mg) in acetonitrile (0.5 mL). The mixture was heated in the microwave at 150° C. for 10 min, filtered in a fritted tube using a Vacmaster multi-filtration apparatus, and purified by preparative-HPLC. 4-(3-Piperidin-1-yl-propyl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile was isolated as a clear gum (12 mg).

Workup

  1. filtrationfiltered in a fritted tube
  2. filtrationa Vacmaster multi-filtration apparatus
  3. custompurified by preparative-HPLC

Sources & evidence

ORD record
ord-3ccf0e01aa2b4fdc877862011b28368d
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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