Isopropylamine → 4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(isopropylamino)pyrimidin-2-ol

HRID 75426Notes

Reaction equation

HRID 75426 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[CH:14]=[C:13](Cl)[N:12]=[C:11]([OH:16])[N:10]=1)[CH2:2]2.[CH:17]([NH2:20])([CH3:19])[CH3:18]>>[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[CH:14]=[C:13]([NH:20][CH:17]([CH3:19])[CH3:18])[N:12]=[C:11]([OH:16])[N:10]=1)[CH2:2]2

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 178517808HCID 178517808, compound

Product 1

HCID 1784567894-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(isopropylamino)pyrimidin-2-ol

Conditions

Temperature
140 °C

Procedure

In a 2-5 mL microwave vial was placed 4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloropyrimidin-2-ol (26, 30 mg, 0.124 mmol) in iPrNH2 (2.5 ml) to give a yellow solution. The reaction was heated under microwave irradiation at 140° C. for 30 min followed by 30 min of heating under microwave irradiation at 160° C. The solvents were removed under reduced pressure. The residue was dissolved in dichloromethane, and purified by silica gel chromatography, using gradient (0-10%) of MeOH in dichloromethane. The title compound was isolated as a yellow solid (20 mg, 61%)

Workup

  1. customto give a yellow solution
  2. temperatureof heating under microwave irradiation at 160° C
  3. customThe solvents were removed under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-03d238cb8bc84486bd2a43f4fafcb5b6
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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