(Diethylamino)sulfur trifluoride → 4-Chloro-6-(2-fluoropropan-2-yl)pyrimidine

HRID 2401199Notes

Reaction equation

CCN(S(F)(F)[F:7])CC.[Cl:10][C:11]1[N:16]=[CH:15][N:14]=[C:13]([C:17](O)([CH3:19])[CH3:18])[CH:12]=1>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]([C:17]([F:7])([CH3:19])[CH3:18])[N:14]=[CH:15][N:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of DAST (0.153 mL, 1.159 mmol) in DCM (5 mL) was added 2-(6-chloro-4-pyrimidinyl)-2-propanol (Intermediate 28, 100 mg, 0.579 mmol) dissolved in DCM (5 mL) dropwise, and the resulting mixture stirred under argon at −78° C. for 4 hrs. The reaction mixture was quenched with excess saturated sodium bicarbonate solution (50 mL) and extracted with DCM (2×20 mL). The organic layers were collected and solvent was removed gently in vacuo. Crude product in DCM was taken into the next reaction without further purification.

Workup

customThe reaction mixture was quenched with excess saturated sodium bicarbonate solution (50 mL)
extractionextracted with DCM (2×20 mL)
customThe organic layers were collected
customsolvent was removed gently in vacuo
customCrude product in DCM was taken into the next reaction without further purification

Sources & evidence

ORD record: ord-3660b335b34844d592d26b9bae16f38b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796283B2

Reaction notes

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