Ammonia → 5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N2-cyclopentyl-N4-(6-methoxypyridin-3-yl)pyrimidine-2,4-diamine

HRID 1811951Notes

Reaction equation

[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[C:10]([C:22]3[N:27]=[C:26]([CH3:28])[N:25]=[C:24](SC)[N:23]=3)=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:31]>O1CCOCC1>[NH2:31][C:24]1[N:25]=[C:26]([CH3:28])[N:27]=[C:22]([C:10]2[C:11]([NH:13][C:14]3[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)=[N:12][C:7]([NH:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:8][CH:9]=2)[N:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A glass microwave reaction vessel was charged with N2-cyclopentyl-N4-(6-methoxypyridin-3-yl)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyrimidine-2,4-diamine (36 mg, 0.085 mmol), ammonia (0.5 mL, 23.11 mmol) and dioxane (2 mL). The reaction mixture was stirred and heated in an oil bath at 100° C. for 24 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with EtOAc to give 5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N2-cyclopentyl-N4-(6-methoxypyridin-3-yl)pyrimidine-2,4-diamine (28 mg, 0.071 mmol, 84% yield). 1H NMR (300 MHz, CDCl3) δ 11.99 (s, 1H); 9.21 (s, 1H); 8.29-8.56 (m, 1H); 8.19 (s, 1H); 6.76 (d, J=8.92 Hz, 1H); 5.26 (s, 3H); 4.25 (s, 1H); 3.95 (s, 3H); 2.49 (s, 3H); 2.04 (s, 2H); 1.34-1.87 (m, 6H). m/z (ESI, +ve ion) 394.1 (M+H)+.

Workup

customA glass microwave reaction vessel
customThe solvent was removed in vacuo
customthe residue was purified by silica gel chromatography
washeluting with EtOAc

Sources & evidence

ORD record: ord-a3b017114b94441d810d294dc97d378b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362241B2

Reaction notes

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