Dimethylbarbituric acid → 2-Methoxy-6-(pyrrolidin-3-YL)pyridine

HRID 2178513Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]2[CH2:13][CH2:12][N:11](CC=C)[CH2:10]2)[N:4]=1.CN1C(=O)CC(=O)N(C)C1=O>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]2[CH2:13][CH2:12][NH:11][CH2:10]2)[N:4]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-methoxy-6-[1-(prop-2-en-1-yl)pyrrolidin-3-yl]pyridine a1-55 (218 mg, 1 mmol, 1 eq) in dichloromethane (3 ml) are added 1,3-dimethylbarbituric acid (470 mg, 3 mmol, 3 eq) and Pd(PPh3)4 (20 mg) and the mixture is warmed overnight at 40° C. The reaction mixture is loaded on an ion exchange acidic resin cartridge, washed with methanol (2×50 ml) and then released with a 1M solution of ammonia in methanol (20 ml) to afford 150 mg of crude 2-methoxy-6-(pyrrolidin-3-yl)pyridine a1-59 that is used in the next step without any further purification.

Workup

washwashed with methanol (2×50 ml)

Sources & evidence

ORD record: ord-6adf50d2cead4ff6b1f437573e985a30
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067930B2

Reaction notes

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