tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(3-methyl-4-oxo-3,4-dihydropteridin-6-yl)piperazine-1-carboxylate

HRID 1959356Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]=[CH:7][N:6]([CH3:12])[C:5]2=[O:13].[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>COCCO>[CH3:12][N:6]1[C:5](=[O:13])[C:4]2[C:9](=[N:10][CH:11]=[C:2]([N:17]3[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]3)[N:3]=2)[N:8]=[CH:7]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6-bromo-3-methyl-pteridin-4-one (17.75 g, 73.64 mmol) in 2-methoxyethanol (163.5 mL) was added tert-butyl piperazine-1-carboxylate (24.70 g, 132.6 mmol) and the resulting suspension heated for 2 hours at 100° C. The reaction mixture was allowed to cool in an ice-water bath and the precipitate that formed collected and washed with cold methanol to give the desired product as a yellow solid (25.08 g, 98% Yield).

Workup

temperatureto cool in an ice-water bath
customthe precipitate that formed
customcollected
washwashed with cold methanol

Sources & evidence

ORD record: ord-3285e419b58149d19c019cf87a83261a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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