Ammonia → 4-(2-Methoxy-4-(6-methoxypyridin-3-ylamino)pyrimidin-5-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1811932Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A glass microwave reaction vessel was charged with 2-methoxy-N-(6-methoxypyridin-3-yl)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyrimidin-4-amine (41 mg, 0.110 mmol), ammonia (0.5 mL, 23.11 mmol) (30% in water) and dioxane (2 mL). The reaction mixture was stirred and heated in an oil bath at 100° C. for 16 h. The solid formed was filtered off and washed with EtOAc to give 4-(2-methoxy-4-(6-methoxypyridin-3-ylamino)pyrimidin-5-yl)-6-methyl-1,3,5-triazin-2-amine (28 mg, 0.082 mmol, 74.5% yield). 1H NMR (300 MHz, d6-DMSO) δ 11.98 (s, 1H); 9.25 (s, 1H); 8.53 (s, 1H); 8.16 (dd, J=8.84, 2.56 Hz, 1H); 7.84 (s, 1H); 7.68 (s, 1H); 6.88 (d, J=8.77 Hz, 1H); 5.76 (s, 1H); 3.89 (s, 3H); 3.86 (s, 3H); 2.40 (s, 3H). m/z (ESI, +ve ion) 341.0 (M+H)+.

Workup

customA glass microwave reaction vessel
customThe solid formed
filtrationwas filtered off
washwashed with EtOAc

Sources & evidence

ORD record: ord-daa54951437245ebab2b34e2392b7bf9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362241B2

Reaction notes

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