(Diethylamino)sulfur trifluoride → 3-(3,4-dimethoxybenzyl)-6-(fluoromethyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

HRID 1022508Notes

Reaction equation

CCN(S(F)(F)[F:7])CC.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:15][N:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH2:27]O)[CH:23]=2)[N:18]([CH:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[C:17]1=[O:35].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:15][N:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH2:27][F:7])[CH:23]=2)[N:18]([CH:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[C:17]1=[O:35]

Participants

Conditions

Temperature: -78 °C

Procedure

0.11 ml of DAST is added dropwise to a solution of 0.1 g of the compound obtained in Step 14.3 in 2 ml of DCM cooled to −78° C. The reaction medium is stirred for 2 hours at −78° C. and then allowed to warm to room temperature. It is neutralized with saturated NaHCO3 solution. The resulting mixture is extracted with DCM. The organic phase is dried over Na2SO4, filtered and evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/EtOAc mixture from (95/5, v/v) to (30/70, v/v) to give 0.032 g of the expected product.

Workup

temperatureto warm to room temperature
extractionThe resulting mixture is extracted with DCM
dry with materialThe organic phase is dried over Na2SO4
filtrationfiltered
customevaporated under reduced pressure
customThe residue is chromatographed on silica gel
washeluting with a DCM/EtOAc mixture from (95/5

Sources & evidence

ORD record: ord-02d958310e694b44b6d0b2401811e1cb
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722659B2

Reaction notes

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