Isopropylamine → 6-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-N-isopropyl-5-nitropyrimidin-4-amine

HRID 75441

Reaction equation

HRID 75441 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH:13]3[O:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)[C:5]([N+:16]([O-:18])=[O:17])=[C:4](Cl)[N:3]=1.[CH:20]([NH2:23])([CH3:22])[CH3:21].C(N(CC)CC)C>ClCCl>[CH:10]12[O:15][CH:13]([CH2:12][CH2:11]1)[CH2:14][N:8]([C:6]1[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([NH:23][CH:20]([CH3:22])[CH3:21])[C:5]=1[N+:16]([O-:18])=[O:17])[CH2:9]2

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 866658963-(2,6-Dichloro-5-nitropyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

Product 1

HCID 866658976-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-N-isopropyl-5-nitropyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(2,6-Dichloro-5-nitropyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (46, 1.53 g, 5.01 mmoles) was dissolved in dichloromethane and added to a solution of isopropylamine (0.512 mL, 6.01 mmoles) in triethylamine (0.909 mL, 6.52 mmoles) and dichloromethane at 0° C. The reaction was allowed to warm to room temperature, stirred for an additional 16 hours, and then concentrated. Purification by chromatography on silica gel (eluting with 0-25% ethyl acetate in hexanes) provided 6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-N-isopropyl-5-nitropyrimidin-4-amine (47) as a yellow solid. Yield: 2.05 g (quantitative yield). LCMS (HP walk-on); 4.54 min., 328.2, M+H.

Workup

  1. concentrationconcentrated
  2. customPurification by chromatography on silica gel (eluting with 0-25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-75c1ad601b1140478613ee0be6c87772
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Linked notes

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