Carbon Tetrachloride → tert-butyl 4-chloro-5H,6H,7H,8H-pyrido(3,4-d)pyrimidine-7-carboxylate

HRID 2406216Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](O)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:39]>ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([Cl:39])=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-hydroxy-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester (1.4 g, 5.6 mmol) and triphenylphosphine (2.9 g, 11.1 mmol) was stirred in DCE (41 mL) until the solution became clear, and then carbon tetrachloride (1.6 mL, 16.7 mmol) was added. The reaction mixture was heated to 70° C. and stirred for 2.5 hours. The volatiles were removed in vacuo and the crude material was directly purified by flash chromatography on silica gel (0-50% EtOAc/heptanes) to afford the title compound as an off-white solid (1.31 g, 87% yield). MS (ESI) m/e (M+H+): 269.73

Workup

customThe volatiles were removed in vacuo
customthe crude material was directly purified by flash chromatography on silica gel (0-50% EtOAc/heptanes)

Sources & evidence

ORD record: ord-ce9839298f824f11b426d1d19e34e739
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809352B2

Reaction notes

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