Methanol → 8-(3,3,4,4,4-Pentafluorobutyl)imidazo[1,5-a]pyrimidine-6-carboximidamide

HRID 2203391Notes

Reaction equation

[NH2:1][Al]CCl.[F:5][C:6]([F:24])([C:20]([F:23])([F:22])[F:21])[CH2:7][CH2:8][C:9]1[N:10]=[C:11]([C:18]#[N:19])[N:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=12.CO>C1(C)C=CC=CC=1>[F:24][C:6]([F:5])([C:20]([F:21])([F:23])[F:22])[CH2:7][CH2:8][C:9]1[N:10]=[C:11]([C:18](=[NH:1])[NH2:19])[N:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=12

Participants

Conditions

Temperature: 107 °C

Procedure

A solution of amino(chloro)methylaluminum (0.5 M in toluene, 18.13 mL, 9.06 mmol) was added quickly to a stirred solution of the intermediate from Step F (0.3006 g, 1.036 mmol) in toluene (12.63 mL) and the mixture was heated at 107° C. overnight. The reaction mixture was cooled to room temperature, MeOH was added and the mixture was stirred for 30 min. The reaction mixture was filtered through a plug of Celite™ (diatomaceous earth), washed through with 2M NH3 in MeOH and the filtrate was concentrated in vacuo to give the crude product. This was purified by flash chromatography using a DCM/MeOH (2 N NH3 in MeOH) gradient to afford the desired product, as a yellow solid. m/z=308.0 (M+H).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe reaction mixture was filtered through a plug of Celite™ (diatomaceous earth)
washwashed through with 2M NH3 in MeOH
concentrationthe filtrate was concentrated in vacuo
customto give the crude product
customThis was purified by flash chromatography

Sources & evidence

ORD record: ord-982ce120367c45d29a4bd3aa2ed2ff8e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365574B2

Reaction notes

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