Ethanol → HCID 90015554, compound

Temperature

-75 °C

To a solution of methyl 4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine-2-carboxylate (which may be prepared by the method described in Description 29) (6.1 g, 20.59 mmol) in dry THF (120 mL) cooled to −75° C. was added diisobutylaluminium hydride (1M in toluene) (41.18 mL, 41.18 mmol) drop-wise over 10 minutes. The solution was stirred at the same temperature for 1.75 h then EtOH (0.96 ml) was added. After 1 minute the reaction mixture was poured into saturated Rochelle salt solution, (250 ml) and water (250 ml). EtOAc (250 ml) was added and the mixture stirred vigorously for 0.5 h then filtered under suction through celite. The filtrate was transferred to a separating funnel and the layers separated. The aqueous fraction was further extracted with EtOAc (200 ml) and the combined organic extracts were dried (MgSO4) and evaporated to a pale yellow, sticky solid. This was stirred with iso-hexane (30 ml) for 5 minutes then sonicated for 5 minutes. It was filtered, washed with iso-hexane (10 ml) and dried at RT under vacuum for 2 hours to give 4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine-2-carbaldehyde (D30) (4.66 g);

1. stirringthe mixture stirred vigorously for 0.5 h
2. filtrationthen filtered under suction through celite
3. customThe filtrate was transferred to a separating funnel
4. customthe layers separated
5. extractionThe aqueous fraction was further extracted with EtOAc (200 ml)
6. dry with materialthe combined organic extracts were dried (MgSO4)
7. customevaporated to a pale yellow, sticky solid
8. stirringThis was stirred with iso-hexane (30 ml) for 5 minutes
9. customthen sonicated for 5 minutes
10. filtrationIt was filtered
11. washwashed with iso-hexane (10 ml)
12. customdried at RT under vacuum for 2 hours

ORD record

ord-1302eea70e2f44ca9f17f64be71a5ef7

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309254B2