Acetonitrile → (8S)-9-(3-methoxybenzyl)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

HRID 80616

Reaction equation

HRID 80616 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]3[NH:17][C@H:16]([C:18]([F:21])([F:20])[F:19])[CH2:15][CH2:14][N:10]3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>CN(C)C=O>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][N:17]1[C:9]2=[N:8][C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:12][C:11](=[O:13])[N:10]2[CH2:14][CH2:15][C@H:16]1[C:18]([F:20])([F:21])[F:19]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 699943-Methoxybenzyl chlorideHCID 136238743(S)-8-(Morpholin-4-yl)-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one

Product 1

HCID 49854200(8S)-9-(3-methoxybenzyl)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-oneYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product is prepared according to the procedure described in Example 22, but using 100 mg of (8S)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one, 57 mg of 1-(chloro-methyl)-3-methoxybenzene and 214 mg of caesium carbonate in 2 ml of dimethylformamide. After treatment, the residue is stirred into acetonitrile. The solid is spin-filter-dried, rinsed with diethyl ether and then dried under a vacuum bell jar. 111 mg of (8S)-9-(3-methoxybenzyl)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one are thus obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customThe solid is spin-filter-dried
  3. washrinsed with diethyl ether
  4. customdried under a vacuum bell jar

Sources & evidence

ORD record
ord-8bea4f97674c497b8b0658e82aa2a9fb
Source dataset
uspto-grants-2014_09
Patent number
US08846670B2

Linked notes

Loading…