Sodium hydride → 7-bromo-4-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yloxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

HRID 532484Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2].[H-].[Na+].[Br:18][C:19]1[C:23]2[N:24]=[CH:25][N:26]=[C:27](Cl)[C:22]=2[N:21]([CH3:29])[CH:20]=1>CN(C=O)C>[Br:18][C:19]1[C:23]2[N:24]=[CH:25][N:26]=[C:27]([O:15][CH:12]3[CH2:11][CH2:10][N:9]([C:6]4[N:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][N:5]=4)[CH2:14][CH2:13]3)[C:22]=2[N:21]([CH3:29])[CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-(5-ethylpyrimidin-2-yl)piperidin-4-ol (93 mg) was added to DMF (5 mL), and cooled to 0° C. Then, NaH (27 mg) was added thereto, and stirred for 30 min. 7-bromo-4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (100 mg) was added thereto, and stirred at room temperature for 12 hours. The reaction mixture was 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

stirringstirred at room temperature for 12 hours
extractionThe reaction mixture was extracted 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-c91c10788d8043fd9ac61cb1650968a8
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853213B2

Reaction notes

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