Triethylamine → tert-Butyl 4-chloro-5,6-dihydropyrido(4',3':4,5)thieno(2,3-d)pyrimidine-7(8H)-carboxylate

HRID 1891027Notes

Reaction equation

O=P(Cl)(Cl)[Cl:3].C(N(CC)CC)C.[C:13]([O:17][C:18]([N:20]1[CH2:32][C:31]2[S:30][C:29]3[N:28]=[CH:27][NH:26][C:25](=O)[C:24]=3[C:23]=2[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(=O)(O)[O-].[Na+]>O>[C:13]([O:17][C:18]([N:20]1[CH2:32][C:31]2[S:30][C:29]3[N:28]=[CH:27][N:26]=[C:25]([Cl:3])[C:24]=3[C:23]=2[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 60 °C

Procedure

To a of mixture of POCl3 (30 mL) and triethylamine (50 mL) at 0° C. was added 4-oxo-3,5,6,8-tetrahydro-4H-9-thia-1,3,7-triaza-fluorene-7-carboxylic acid tert-butyl ester (10.0 g). The reaction mixture was heated at 60° C. for 3 h. Water was then added, followed by sodium bicarbonate to neutralize the reaction mixture. The resulting mixture was extracted with dichloromethane. The organic layer was concentrated and the crude compound was purified by silica gel column chromatography using a mixture of hexanes:ethyl acetate (10:1) to give the title compound (3.1 g, 25%). 1H NMR (400 MHz, CDCl3): δ 8.70 (s, 1H), 4.69 (s, 2H), 3.74 (t, 2H, J=5.6 Hz), 3.14-3.18 (brs, 2H), 1.46 (s, 9H). LC-MS (ESI) m/z 326.0 (M+H).

Workup

extractionThe resulting mixture was extracted with dichloromethane
concentrationThe organic layer was concentrated
customthe crude compound was purified by silica gel column chromatography
additiona mixture of hexanes:ethyl acetate (10:1)

Sources & evidence

ORD record: ord-39d9b34cc235440daf0d44438346db97
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507502B2

Reaction notes

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