Potassium Carbonate → tert-butyl 4-(7-bromo-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)piperidine-1-carboxylate

HRID 532481Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To 7-bromo-4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (200 mg) obtained in Step 4-4 of Preparation Example 4, t-butyl 4-hydroxypiperidine-1-carboxylate (180 mg), K2CO3 (168 mg) and N,N-dimethylformamide (4 ml) were added, and stirred at 100° C. for 12 hours in a hermetically sealed reactor. The reaction mixture was cooled to room temperature, extracted with ethyl acetate and distilled water, and the organic layer thus obtained was washed with water and a saline solution. Subsequently, the washed organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound.

Workup

additionwere added
temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate
distillationdistilled water
customthe organic layer thus obtained
washwas washed with water
dry with materialSubsequently, the washed organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-1842d083bfee42a190eadb7ea630c9e3
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853213B2

Reaction notes

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