Ammonia → 5,6-Dichloro-2-cyclopropylpyrimidine-4-carboxylic acid

HRID 249655Notes

Reaction equation

P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[C:12](=O)[NH:11][C:10]([CH:14]2[CH2:16][CH2:15]2)=[N:9][C:8]=1[C:17]([OH:19])=[O:18].N>C(#N)C>[Cl:6][C:7]1[C:8]([C:17]([OH:19])=[O:18])=[N:9][C:10]([CH:14]2[CH2:16][CH2:15]2)=[N:11][C:12]=1[Cl:3]

Participants

Conditions

Temperature: 85 °C

Procedure

Phosphorus oxychloride (14 mL, 23 g, 0.15 mol) and 5-chloro-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (i.e. the product of Step B1 or B2) (75 g, 300 mmol) were combined and heated at 85° C. for 3 h. The reaction mixture was cooled to 30° C. and added over 30 minutes to a mixture of acetonitrile (50 mL) and ice water (80 mL), with the temperature maintained at 5-10° C. and the pH maintained in the range 1-3 by co-feeding aqueous ammonia (28%). The pH was adjusted to about 2, the mixture was concentrated at 25° C. with a rotary evaporator to remove acetonitrile, and the precipitated product was isolated by filtration and washed with water (2×25 mL). The solid was dried in a vacuum oven to afford the title compound (ca. 7.0 g).

Workup

temperatureThe reaction mixture was cooled to 30° C.
temperaturemaintained at 5-10° C.
concentrationthe mixture was concentrated at 25° C. with a rotary evaporator
customto remove acetonitrile
customthe precipitated product was isolated by filtration
washwashed with water (2×25 mL)
customThe solid was dried in a vacuum oven

Sources & evidence

ORD record: ord-e706e34adbfd42c5aa7543492c59f71d
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863220B2

Reaction notes

Loading…