Acetonitrile → [1-(3-Amino-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-7-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

HRID 729422Notes

Reaction equation

[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([F:14])[C:11](Cl)=[N:12][C:5]=2[N:4]([CH:15]2[CH2:17][CH2:16]2)[C:3]1=[O:18].[C:19]([O:23][C:24](=[O:31])[NH:25][C@H:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20].C(N(CC)C(C)C)(C)C.C(#N)C>O>[C:19]([O:23][C:24](=[O:31])[NH:25][CH:26]1[CH2:30][CH2:29][N:28]([C:11]2[C:10]([F:14])=[CH:9][C:6]3[C:7](=[O:8])[N:2]([NH2:1])[C:3](=[O:18])[N:4]([CH:15]4[CH2:17][CH2:16]4)[C:5]=3[N:12]=2)[CH2:27]1)([CH3:22])([CH3:20])[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 0.11 g (0.4 mmol) of 3-amino-7-chloro-1-cyclopropyl-6-fluoro-1H-pyrido[2,3-d]pyrimidine-2,4-dione (Example 24b), 0.105 g (0.56 mmol) of (S)-3-pyrrolidinylcarbamic acid tert-butyl ester (J. Med. Chem., 1992; 35:1764), 1.2 mL of N,N-diisopropylethylamine and 3 mL of acetonitrile is heated at 50° C. for 18 hours. The reaction mixture is diluted with 9 mL of water, cooled to 0° C. and the solid is removed by filtration, washed with 50% aqueous acetonitrile and dried in vacuo to give 0.14 g of the title compound, mp 108-110° C.

Workup

customthe solid is removed by filtration
washwashed with 50% aqueous acetonitrile
customdried in vacuo

Sources & evidence

ORD record: ord-c520c58138fd422d8872fda79af0a5b4
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582627B2

Reaction notes

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