2-Chloropyrimidine → HCID 69099810, compound

HRID 2251489Notes

Reaction equation

HRID 2251489 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:25])([CH3:24])[CH2:10][NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.Cl[C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1.CCN(C(C)C)C(C)C>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:25])([CH3:24])[CH2:10][N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:22])([F:21])[F:23])=[CH:15][CH:14]=2)[C:27]2[N:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 46703552HCID 46703552, compound

Product 1

HCID 69099810HCID 69099810, compoundYield 88.1%

Procedure

Condensation N-[2-(4-methoxyphenyl)-2-methylpropyl]-N-[4-(trifluoromethoxy)benzyl]amine (250 mg; 0.71 mmol) with 2-chloro-pyrimidine (85 mg; 0.74 mmol) as per general procedure E (2 eq DIEA, 210C, 14 hr) afforded N-[2-(4-methoxyphenyl)-2-methylpropyl]-N-[4-(trifluoromethoxy)benzyl]pyrimidin-2-amine (270 mg; 88% yield). MS: m/z 432 (M+1).

Sources & evidence

ORD record
ord-6172996d2a34410094f6acbb8fb2a5b9
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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