Dichloromethane → Tert-butyl 4-(5-chloropyrimidin-2-yl)benzylcarbamate

HRID 1848720Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C(Cl)Cl.[C:12]([O:16][C:17]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[Na+].[Na+]>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.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[C:12]([O:16][C:17](=[O:18])[NH:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:2]2[N:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=2)=[CH:25][CH:26]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

To a 10 mL microwave vial were added 2,5-dichloropyrimidine (285 mg, 1.8 mmol), Pd(dppf)Cl2.DCM (45 mg, 0.05 mmol), (4-(((tert-butoxycarbonyl)amino)methyl)phenyl)boronic acid (419 mg, 1.67 mmol), Na2CO3 (2 mL, 2M) and 1,4-dioxane (7 mL). The vial was flushed with N2 then capped and placed in a heating block and heated at 80° Celsius. After 6 h, the resulting mixture cooled to RT and transferred to a round-bottomed flask and concentrated to dryness. The residue was purified using FCC to provide 376 mg of the title compound. MS (ESI): mass calcd. for C16H18ClN3O2, 319.11; m/z found 320.1 [M+H]+.

Workup

customThe vial was flushed with N2
customthen capped
temperaturethe resulting mixture cooled to RT
customtransferred to a round-bottomed flask
concentrationconcentrated to dryness
customThe residue was purified

Sources & evidence

ORD record: ord-21e6ddde78e740d5afc5162e6302a285
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952177B2

Reaction notes

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