Hydrochloric Acid → 4-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

HRID 747124Notes

Reaction equation

CC1(C)C2C(=CC(N[C:12]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=4)[N:15]=[CH:14][N:13]=3)=CC=2)N(C(=O)C)C1.CC1(C)C2C(=CC([N+]([O-])=O)=CC=2)NC1C(=O)C.O.O.[Sn](Cl)[Cl:52].Cl>C(OCC)C>[Cl:52][C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:15]=[CH:14][N:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-{3,3-Dimethyl-6-[6-(4-trifluoromethylphenyl)pyrimidin-4-ylamino]-2,3-dihydroindol-1-yl}ethanone. To a solution of 1-(3,3-dimethyl-6-nitro-2,3-dihydroindol-yl)ethanone (110 mg, 0.47 mmol) in ethyl ether (3 mL), magnetically stirred in a round-bottomed flask at 0° C., was added tin (II) chloride dihydrate (0.67 g, 2.96 mmol, Aldrich) and concd HCl (0.3 mL). The reaction mixture was stirred at 0° C. for 10 min, allowed to warm to 25° C. then stirred at that temperature overnight. The reaction mixture was washed with 10 N NaOH (10 mL), extracted with EtOAc and concentrated in vacuo. Analogous to the procedure used to prepare Example 5(b), the crude product and 4-chloro-6-(4-trifluoromethylphenyl)pyrimidine, Example 5(a), (0.19 g, 0.75 mmol) provided, after purification by silica gel chromatography (3:2 hexanes/EtOAc), the title product. MS (ESI, pos. ion) m/z: 427 (M+1). MP: 227-230° C.

Workup

temperatureto warm to 25° C.
stirringthen stirred at that temperature overnight
washThe reaction mixture was washed with 10 N NaOH (10 mL)
extractionextracted with EtOAc
concentrationconcentrated in vacuo
customto prepare Example 5(b)

Sources & evidence

ORD record: ord-8616ecbf336e40bdbe39bd43ccc5eb58
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396831B2

Reaction notes

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