Water → 2-[(Adamantan-1-ylmethyl)amino]pyrimidine-5-carboxylic acid (4-fluorophenyl)amide

HRID 348434Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14](SC)=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.O1CCOCC1.O.[C:26]12([CH2:36][NH2:37])[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2.O>Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([NH:37][CH2:36][C:26]34[CH2:35][CH:30]5[CH2:29][CH:28]([CH2:34][CH:32]([CH2:31]5)[CH2:33]3)[CH2:27]4)=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (50 mg, 0.19 mmol) in 4/1 dioxane/water (0.6 mL) in a sealed tube was added 1-adamantanemethyl amine (250 μL, 1.4 mmol). The solution was heated at 110° C. for 18 h, cooled, diluted with 3% HCl and then poured into water to form a precipitate. The solids were collected by filtration, washed with water and dried. Trituration of the solids with ethyl acetate at about 70° C., followed by a hot filtration and washing with hexane, afforded 16.7 mg (24% yield) of the titled product as a white solid. API-MS m/z 381 (MH)+, 379 (M−H)−.

Workup

temperaturecooled
customto form a precipitate
filtrationThe solids were collected by filtration
washwashed with water
customdried
filtrationTrituration of the solids with ethyl acetate at about 70° C., followed by a hot filtration
washwashing with hexane

Sources & evidence

ORD record: ord-087eb19b4826491ab5c92150505c6302
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176310B1

Reaction notes

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