Malononitrile → HCID 68642337, compound

HRID 403525Notes

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[CH:14]=[CH:13][O:12][N:11]=2)=[CH:8][C:7]([C:15](=[NH:17])[NH2:16])=[N:6]1.[C:22](#[N:26])[CH2:23][C:24]#[N:25]>C(O)C>[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[CH:14]=[CH:13][O:12][N:11]=2)=[CH:8][C:7]([C:15]2[N:16]=[C:24]([NH2:25])[CH:23]=[C:22]([NH2:26])[N:17]=2)=[N:6]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1-(2-fluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazole-3-carboximidamide (50 mg, 0.18 mmol) in ethanol (2 mL) was added malononitrile (35 mg, 0.53 mmol). After heating the solution to 110° C. for 6 hours, the solvent was removed in vacuo to give the crude product as a red oil. Purification by silica gel chromatography (0-10% methanol in dichloromethane) gave 2-(1-(2-fluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)pyrimidine-4,6-diamine (I-103, 20 mg, 0.056 mmol, 32% yield) as a pink solid. 1H NMR (400 MHz, CDCl3) δ 8.45 (d, 1H), 7.31 (s, 1H), 7.19-7.14 (m, 1H), 7.01-6.96 (m, 1H), 6.92 (t, 1H), 6.74-6.71 (m, 1H), 6.58 (d, 1H), 5.90 (s, 2H), 5.57 (s, 1H), 5.03 (br s, 4H).

Workup

customthe solvent was removed in vacuo
customto give the crude product as a red oil
customPurification by silica gel chromatography (0-10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-245e4326193a4bb8b7c444d076a83c3f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748442B2

Reaction notes

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