HCID 66611727, compound → HCID 59548261, compound

HRID 1621696Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]([C:15]3[N:20]=[C:19]([CH3:21])[N:18]=[C:17]([N:22](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)[N:16]=3)=[CH:13][CH:12]=[C:11]([CH3:41])[N:10]=2)[CH:5]=[N:6][CH:7]=1>C(O)(C(F)(F)F)=O.OS(C(F)(F)F)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]([C:15]3[N:20]=[C:19]([CH3:21])[N:18]=[C:17]([NH2:22])[N:16]=3)=[CH:13][CH:12]=[C:11]([CH3:41])[N:10]=2)[CH:5]=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-(2-(5-fluoropyridin-3-ylamino)-6-methylpyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (118 mg, 0.214 mmol) in 2 mL of TFA was treated with 2 drops of triflic acid. The brown solution was heated in an oil bath at 80° C. for 8 h. The solution was concentrated and the residue was stirred in 5 mL of EtOAc and 2 mL of 0.5N NaOH. The precipitated solid was collected by filtration, rinsed with 2×2 mL of water, followed by 2 mL of EtOAc and 2×2 mL of DCM. The yellow crystalline solid was collected and dried in a vacuum oven at 40° C. for 18 h to give 4-(2-(5-fluoropyridin-3-ylamino)-6-methylpyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (60 mg, 0.193 mmol, 90% yield). 1H NMR (400 MHz, d6-DMSO) δ 12.33 (1H, s); 8.66 (1H, s); 8.73 (1H, d, J=8.2 Hz); 8.60 (1H, d, J=12.9 Hz); 8.16 (1H, s); 7.90 (1H, br.); 7.75 (1H, br.); 6.91 (1H, d, J=8.0 Hz); 2.48 (3H, s); 2.44 (3H, s). m/z (ESI, +ve ion) 312 (M+H)+.

Workup

concentrationThe solution was concentrated
filtrationThe precipitated solid was collected by filtration
washrinsed with 2×2 mL of water
customThe yellow crystalline solid was collected
customdried in a vacuum oven at 40° C. for 18 h

Sources & evidence

ORD record: ord-a26b1aed464744b3b691fb0614937f0c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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