Methanol → HCID 86696688, compound

HRID 1774190Notes

Reaction equation

I[Si](C)(C)C.[F:6][C:7]1[C:8]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[N:16]=2)=[CH:9][C:10]([O:13]C)=[N:11][CH:12]=1.CO.C([O-])(O)=O.[Na+]>C(#N)C>[F:6][C:7]1[C:8]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[N:16]=2)=[CH:9][C:10](=[O:13])[NH:11][CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Iodotrimethylsilane (0.186 mL, 1.30 mmol) was added dropwise to a solution of 4-(5-fluoro-2-methoxypyridin-4-yl)-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-2-amine (0.0992 g, 0.3260 mmol) in acetonitrile (6 mL) in a vial at room temperature. The sealed vial was heated at 80° C. overnight. The reaction mixture was treated with MeOH (about 2 mL) and some saturated aqueous NaHCO3. The mixture was concentrated, and the aqueous residue was treated dropwise with 1M HCl until a tan precipitate formed (pH 2). This was extracted with 2 portions 10% isopropyl alcohol (“IPA”) in DCM. The combined organics were dried over MgSO4, filtered, and evaporated to yield 5-fluoro-4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (0.0293 g, 0.1009 mmol, 30.96% yield) as a solid.

Workup

concentrationThe mixture was concentrated
additionthe aqueous residue was treated dropwise with 1M HCl until a tan precipitate
customformed (pH 2)
extractionThis was extracted with 2 portions 10% isopropyl alcohol (“IPA”) in DCM
dry with materialThe combined organics were dried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-0cf5f7b53b854510a1be07fa0eb5a4f2
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09259470B2

Reaction notes

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