Methyl iodide → N2-(2-chloro-4-(2-methyl-2H-tetrazol-5-yl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine

HRID 1630336Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14]1[N:19]=[C:18]([NH:20][CH3:21])[C:17]([C:22]([F:25])([F:24])[F:23])=[CH:16][N:15]=1.[C:26]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[N:11][N:10]([CH3:26])[N:9]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14]1[N:19]=[C:18]([NH:20][CH3:21])[C:17]([C:22]([F:24])([F:25])[F:23])=[CH:16][N:15]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of N2-(2-chloro-4-(2H-tetrazol-5-yl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine (80 mg, 0.22 mmol), K2CO3 (45 mg, 0.32 mmol) and methyl iodide (15 uL, 0.24 mmol) in acetone (2 mL) was heated at 40° C. for 1 h. The mixture was cooled and filtered. The filtrate was concentrated under reduced pressure and the crude residue purified via silica gel column chromatography (0-100% ethyl acetate/isohexane) to give N2-(2-chloro-4-(2-methyl-2H-tetrazol-5-yl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine (58 mg, 70%). LCMS (10 cm_ESCI_Formic_MeCN): [MH+]=385 at 4.31 min. 1H NMR (400 MHz, CDCl3): δ 8.76 (d, J=8.7, 1H); 8.23-8.19 (m, 2H); 8.05 (dd, J=8.7, 2.0, 1H); 7.72 (s, 1H); 5.29 (s, 1H); 4.40 (s, 3H); 3.12 (d, J=4.7, 3H).

Workup

temperatureThe mixture was cooled
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customthe crude residue purified via silica gel column chromatography (0-100% ethyl acetate/isohexane)

Sources & evidence

ORD record: ord-2d511904ff2440a2b13d04ab9fb86ec7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791130B2

Reaction notes

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