5-benzyl-1H-1,2,4-triazol-3-amine → 2-benzyl-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one

HRID 923343Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5-benzyl-2H-1,2,4-triazol-3-amine (174 mg, 1.00 mmol, 1.00 equiv), acetic acid (3 mL), and ethyl 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-oxopropanoate (275 mg, 1.10 mmol, 1.10 equiv) was stirred overnight at 110° C. The reaction was concentrated to dryness and purified with prep-TLC (MeOH:DCM=1:30) to afford 30.7 mg (8%) of 2-benzyl-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a yellow solid.

Workup

concentrationThe reaction was concentrated to dryness
custompurified with prep-TLC (MeOH:DCM=1:30)

Sources & evidence

ORD record: ord-9de92dc3092844de8a6364eed6ebc56a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278973B2

Reaction notes

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