Sodium Carbonate → HCID 68299326, compound

HRID 532498Notes

Reaction equation

Br[C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([NH:11][CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:5]=2[N:4]([CH3:25])[CH:3]=1.[CH3:26][S:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)(=[O:29])=[O:28].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[CH3:25][N:4]1[C:5]2[C:10]([NH:11][CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[N:9][CH:8]=[N:7][C:6]=2[C:2]([C:33]2[CH:34]=[CH:35][C:30]([S:27]([CH3:26])(=[O:29])=[O:28])=[CH:31][CH:32]=2)=[CH:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

tert-butyl 4-(7-bromo-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl amino)piperidin-1-carboxylate, 73 mg of 4-methanesulfonyl-phenylboronic acid, 17 mg of Pd(PPh3)4 and 0.73 ml of 2N Na2CO3 were added in 3 ml of 1,4-dioxane and stirred in a closed reactor at 100° C. for 12 hr. The resulting mixture was cooled to room temperature, extracted with ethylacetate and distilled water. The organic layer was washed with water and saline solution, dried over anhydrous sodium sulfate and concentrated under a reduced pressure to obtain 15 mg of the title compound.

Workup

temperatureThe resulting mixture was cooled to room temperature
extractionextracted with ethylacetate
distillationdistilled water
washThe organic layer was washed with water and saline solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record: ord-e0fe0ad8debc4884ae7760ccbdd9ec1a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853213B2

Reaction notes

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