Sodium Carbonate → tert-Butyl 6-[2-(cyclopropyl)pyrimidin-5-yl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 1441484Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][CH2:12]3)O1.CC1(C)C(C)(C)OB(C2C=CC=C3C=2CN(C(OC(C)(C)C)=O)CC3)O1.Br[C:54]1[CH:55]=[N:56][C:57]([CH:60]2[CH2:62][CH2:61]2)=[N:58][CH:59]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].CCO.C1(C)C=CC=CC=1>[CH:60]1([C:57]2[N:58]=[CH:59][C:54]([C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[CH2:15][N:14]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:13][CH2:12]4)=[CH:55][N:56]=2)[CH2:62][CH2:61]1

Participants

Conditions

Temperature: 81 °C

Procedure

A 4:1 mixture (0.097 g, 0.27 mmol) of tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate and tert-butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, 5-bromo-2-cyclopropylpyrimidine (0.054 g, 0.27 mmol), PdCl2×dppf (0.0045 g), 2M sodium carbonate (1.0 mL), toluene (4.0 mL) and EtOH (1.0 mL) was purged with dry argon for ten minutes, then heated in a sealed vial at 81° C. for 6 h. The black solution was filtered through glass-wool, taken up in water-brine and washed twice with EtOAc. The combined organic phases were dried, filtered and concentrated with silica (5 g). Column chromatography with EtOAc-heptanes (1:5 through 1:2) gave 0.034 g (36%) of the title product as white solid.

Workup

filtrationThe black solution was filtered through glass-wool
washwashed twice with EtOAc
customThe combined organic phases were dried
filtrationfiltered
concentrationconcentrated with silica (5 g)

Sources & evidence

ORD record: ord-51808fde009c45aebda85141743d9d83
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655664B2

Reaction notes

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