HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

3-Iodotoluene → (8S)-9-(3-methylphenyl)-2-(morpholin-4-yl)-8-(trifluoro-methyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

HRID 80623
Notes
Print preview

Reaction equation

HRID 80623 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.I[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C@H]1(N)CCCC[C@@H]1N>CN(C)C=O.[Cu](I)I.C(Cl)Cl.CO.C(Cl)Cl>[CH3:29][C:25]1[CH:24]=[C:23]([N:17]2[C:9]3=[N:8][C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:12][C:11](=[O:13])[N:10]3[CH2:14][CH2:15][C@H:16]2[C:18]([F:20])([F:21])[F:19])[CH:28]=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 122683-IodotolueneHCID 62657Potassium Phosphate, TribasicHCID 4793071,2-Diaminocyclohexane, (+)-HCID 136238743(S)-8-(Morpholin-4-yl)-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one

Product 1

HCID 49854400(8S)-9-(3-methylphenyl)-2-(morpholin-4-yl)-8-(trifluoro-methyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

The product is prepared according to the procedure described in Example 12, but using 250 mg of (8S)-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one (Example 1e) in 4 ml of dimethylformamide, 251 mg of 1-iodo-3-methylbenzene, 349 mg of tripotassium phosphate, 156 mg of copper iodide and 93 mg of (1S,2S)-cyclo-hexane-1,2-diamine. After 1 hour at 150° C. under microwave irradiation and silica column purification of the resulting reaction mixture (elution gradient of CH2Cl2 to CH2Cl2/MeOH 98/02), 195 mg of (88)-9-(3-methylphenyl)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]-pyrimidin-4-one are obtained in the form of a green solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customare obtained in the form of a green solid

Sources & evidence

ORD record
ord-072e0694c5ce44418a2b16a7001210a6
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846670B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes