Sodium Hydroxide → [4-(5-Pyridin-4-yl-thiophen-2-yl)-pyrimidin-2-yl]-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

HRID 1434945Notes

Reaction equation

Br[C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH:14]3[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[CH2:15]3)[N:8]=2)=[CH:4][CH:3]=1.C[Sn](C)(C)[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.[OH-].[Na+]>C1(C)C(C)=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:29]1[CH:30]=[CH:31][C:26]([C:2]2[S:6][C:5]([C:7]3[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH:14]4[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[CH2:15]4)[N:8]=3)=[CH:4][CH:3]=2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 120 °C

Procedure

[4-(5-Bromo-thiophen-2-yl)-pyrimidin-2-yl]-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (Step C of Example 5, 100 mg, 0.253 mmol), 4-trimethylstannylpyridine (186 mg, 0.506 mol) and PdCl2(PPh3)2 (18 mg, 0.025 mmol) were dissolved in xylene (5 ml) and heated to 120° C. for 30 minutes. The reaction mixture was poured on 1N-NaOH and extracted three times with EtOAc. The combined organic phases were dried over sodium sulfate, filtered, evaporated to dryness and purified via preparative HPLC to give the title compound as yellow crystals. Yield: 23 mg (23%)

Workup

extractionextracted three times with EtOAc
dry with materialThe combined organic phases were dried over sodium sulfate
filtrationfiltered
customevaporated to dryness
custompurified via preparative HPLC

Sources & evidence

ORD record: ord-4cc9727f6de6431db3cebf7521910d31
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615562B2

Reaction notes

Loading…