Triethylamine → (8S)-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one

HRID 633739Notes

Reaction equation

HRID 633739 reaction equation
Cl[C:2]1[N:3]=[C:4]2[NH:12][C@H:11]([C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.[CH:17]12[O:24][CH:21]([CH2:22][CH2:23]1)[CH2:20][NH:19][CH2:18]2.C(N(CC)CC)C>>[CH:21]12[O:24][CH:17]([CH2:23][CH2:22]1)[CH2:18][N:19]([C:2]1[N:3]=[C:4]3[NH:12][C@H:11]([C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:9][N:5]3[C:6](=[O:8])[CH:7]=1)[CH2:20]2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 120692318-Oxa-3-azabicyclo[3.2.1]octaneHCID 136238740(S)-8-chloro-2-(trifluoromethyl)-3,4-dihydro-1H-pyrimido[1,2-a]pyrimidin-6(2H)-one

Product 1

HCID 136950337(8S)-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-oneYield 92.2%

Procedure

500 mg (1.97 mmol) of (8S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, 884 mg (5.91 mmol) of 8-oxa-3-azabicyclo[3.2.1]octane and 820 μl (5.91 mmol) of triethylamine are placed in a microwave tube. The mixture is irradiated for 10 minutes at 150° C. The reaction medium is purified directly by passing through an RP18 reverse-phase column (eluent: H2O: 100% to CH3CN: 100%) to give 600 mg of (8S)-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, the characteristics of which are as follows:

Workup

  1. customThe mixture is irradiated for 10 minutes at 150° C
  2. customThe reaction medium is purified directly

Sources & evidence

ORD record
ord-d48e3bf56a144c689f7c498d1c43ced3
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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