1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86685304, compound

HRID 1852972Notes

Reaction equation

HRID 1852972 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][NH:16][CH:17]=3)[N:10]3[CH:18]=[CH:19][N:20]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1.[C:21]([O:30][CH3:31])(=[O:29])/[CH:22]=[CH:23]/[CH2:24][C:25]([O:27][CH3:28])=[O:26].C1CCN2C(=NCCC2)CC1>CC#N>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH:23]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:22][C:21]([O:30][CH3:31])=[O:29])[CH:17]=3)[N:10]3[CH:18]=[CH:19][N:20]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5271579Dimethyl glutaconateHCID 674525377-(1-methyl-1H-pyrazol-4-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

Product 1

HCID 86685304HCID 86685304, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

7-(1-Methyl-1H-pyrazol-4-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation K; 0.165 g, 0.622 mmol) was suspended in CH3CN (5 mL) and (E)-dimethyl pent-2-enedioate (0.295 g, 1.87 mmol) was added followed by DBU (0.0947 g, 0.622 mmol). The reaction was warmed to 55° C. and heated for 9 hours. The reaction was then cooled and concentrated. The residue was purified on silica gel (1-4% methanol in DCM) to afford dimethyl 3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)pentanedioate (205 mg, 78% yield). MS (apci) m/z=424.2 (M+H).

Workup

  1. temperatureheated for 9 hours
  2. temperatureThe reaction was then cooled
  3. concentrationconcentrated
  4. customThe residue was purified on silica gel (1-4% methanol in DCM)

Sources & evidence

ORD record
ord-8f4a3ad5566d4146abd7e9b2d9b8e9e3
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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