5-Bromopyrimidine → 4-(Pyrimidin-5-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726299Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[NH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.C(O[Na])(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][CH:9]([NH:8][C:2]2[CH:3]=[N:4][CH:5]=[N:6][CH:7]=2)[CH2:10][CH2:11]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 5-bromopyrimidine (325 mg, 2.04 mmol), 4-amino-1-Boc-piperidine (425 mg, 2.12 mmol), Pd2(dba)3 (41 mg, 0.045 mmol), (±)-BINAP (78 mg, 0.13 mmol) and t-BuONa (210 mg, 2.19 mmol) in freshly degassed toluene (7.0 mL) was stirred at 85° C. under argon for 2 hours. Basic work-up and purification gave 4-(pyrimidin-5-ylamino)-piperidine-1-carboxylic acid tert-butyl ester as a pale brown solid (415 mg, 73%).

Workup

customBasic work-up and purification

Sources & evidence

ORD record: ord-81bed1ea779e4b80bfa9bbd0f36a06e6
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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