Water → HCID 178508679, compound

HRID 729920Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:23]=[CH:22][C:12]([O:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=3)=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1.[N-:30]=[N+:31]=[N-:32].[Na+].C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[C:24]1([C:4]2[N:3]=[C:2]([NH2:1])[N:7]=[C:6]([NH:8][C:9]3[CH:23]=[CH:22][C:12]([O:13][C:14]4[CH:19]=[CH:18][N:17]=[C:16]([C:20]5[NH:32][N:31]=[N:30][N:21]=5)[CH:15]=4)=[CH:11][CH:10]=3)[CH:5]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-{4-[(2-amino-6-phenylpyrimidin-4-yl)amino]phenoxy}pyridine-2-carbonitrile (0.20 g, 0.53 mmol, prepared in Example 8), sodium azide (0.051 g, 0.79 mmol), and triethylamine (0.11 g, 0.79 mmol) in toluene (15 mL) was heated at 100° C. for 2 days. The mixture was then treated with cold water. The solid was collected by filtration, washed with water and methanol to give pure product, 0.14 g (63%). 1H NMR (DMSO-d6) δ 9.51 (s, 1H), 8.62 (d, 1H), 7.94 (m, 4H), 7.55 (d, 1H), 7.48 (m, 3H), 7.19 (m, 3H), 6.48 (m, 3H); MS ES 424 (M+H)+ calc 424.

Workup

filtrationThe solid was collected by filtration
washwashed with water and methanol
customto give pure product, 0.14 g (63%)

Sources & evidence

ORD record: ord-d176f53668a44c53be5caa4995334df9
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582645B2

Reaction notes

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