3-Ethoxy-2-propenenitrile → 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyrimidin-4-amine

HRID 2174292Notes

Reaction equation

[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15](=[NH:17])[NH2:16])=[N:6]1.C(O[CH:25]=[CH:26][C:27]#[N:28])C.C1CCN2C(=NCCC2)CC1.CC#N.CO.C(Cl)Cl>N1C=CC=CC=1>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15]2[N:16]=[C:27]([NH2:28])[CH:26]=[CH:25][N:17]=2)=[N:6]1

Participants

Conditions

Temperature: 110 °C

Procedure

To 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboximidamide (Intermediate-6, 0.33 mmol) was added a stock solution of 3-ethoxyacrylonitrile (3 equiv) and DBU (1 equiv) in pyridine (3 mL). The reaction was warmed to 110° C. and stirred for 46 h. The reaction mixture was conc. and purified using SiO2 chromatography and an appropriate gradient (CH3CN/MeOH/CH2Cl2) to afford 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyrimidin-4-amine (I-48) as a light tan solid (78% yield).

Workup

custompurified

Sources & evidence

ORD record: ord-a8e17d6c869f4ac0bc21c55383ac4360
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061030B2

Reaction notes

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