Potassium Carbonate → 7-chloro-5-(4-(hydroxymethyl)thiazol-2-ylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1023308Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][OH:8])[N:6]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:16]1[C:25]2[C:24](=[O:26])[N:23]([CH3:27])[CH:22]=[N:21][C:20]=2[CH:19]=[C:18]([Cl:28])[N:17]=1>O1CCOCC1>[Cl:28][C:18]1[N:17]=[C:16]([NH:1][C:2]2[S:3][CH:4]=[C:5]([CH2:7][OH:8])[N:6]=2)[C:25]2[C:24](=[O:26])[N:23]([CH3:27])[CH:22]=[N:21][C:20]=2[CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(2-aminothiazol-4-yl)methanol (70.0 mg, 0.54 mmol) and K2CO3 (148.6 mg, 1.08 mmol) were added to a solution of 5,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (123.7 mg, 0.54 mmol) in 1,4-dioxane (2.7 mL). The reaction mixture was heated at 80° C. overnight, cooled down, quenched with H2O (20 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, concentrated, and purified by silica gel chromatography (10% methanol/dichloromethane) to give 7-chloro-5-(4-(hydroxymethyl)thiazol-2-ylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one as a white solid product.

Workup

temperaturecooled down
customquenched with H2O (20 mL)
extractionextracted with ethyl acetate (3×5 mL)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
custompurified by silica gel chromatography (10% methanol/dichloromethane)

Sources & evidence

ORD record: ord-517d9d400b8349ce8496b034e21a2a6c
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722692B2

Reaction notes

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