Triethylamine → 2-Chloro-4-(2-hydroxy-2-methylpropylamino)pyrimidine-5-carboxylic acid

HRID 871874

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.[NH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15].C(N(CC)CC)C.C(OCC)(=O)C>C1COCC1.O>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][CH2:13][C:14]([OH:16])([CH3:17])[CH3:15])[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 3.5 °C

Procedure

A suspension of 19.9 g (86.73 mmol) of 2,4-dichloro-5-pyrimidinecarboxylic acid in 155 mL of THF is cooled on an ice bath to 2-5°C., and a solution of 8.5 g (95.40 mmol) of 1-amino-2-methyl-2-propanol and 36.3 mL (260.19 mmol) of triethylamine in 60 mL of THF is added dropwise. The mixture is stirred at room temperature overnight. Ethyl acetate and water are added. After separation of the phases by settling, the aqueous phase is acidified with aqueous 1N HCl solution to pH 2. The precipitate is isolated by filtration to give 12.6 g of the expected product in the form of a pale yellow solid, which is used as obtained in the following step. Yield=59%.

Workup

customAfter separation of the phases
customThe precipitate is isolated by filtration

Sources & evidence

ORD record: ord-f1b8463a504b4795b4911c5acf111e44
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975250B2

Linked notes

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