Aminopyrazine → HCID 86659388, compound

HRID 1187690Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH3:10])[CH:5]=[C:4]([C:18]2[CH:19]=[N:20][N:21]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=2)[CH:3]=1.[NH2:31][C:32]1[CH:37]=[N:36][CH:35]=[CH:34][N:33]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+]>>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C@@H:9]([NH:8][C:6]2[CH:5]=[C:4]([C:18]3[CH:19]=[N:20][N:21]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=3)[CH:3]=[C:2]([NH:31][C:32]3[CH:37]=[N:36][CH:35]=[CH:34][N:33]=3)[N:7]=2)[CH3:10])=[CH:12][CH:13]=1

Participants

Reactant 4

HCID 78747Aminopyrazine

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

HCID 23676156Sodium t-butoxide

HCID 86659386HCID 86659386, compound

Product 1

HCID 86659388HCID 86659388, compoundYield 91%

Conditions

Temperature: 100 °C

Procedure

68 mg of (S)-6-chloro-N-[1-(4-fluorophenyl)ethyl]-4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-4-yl)pyridine-2-amine obtained by Step 3, 17 mg of 2-aminopyrazine, 15 mg of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 21 mg of sodium t-butoxide and 8 mg of tris(dibenzylideneacetone)(chloroform)dipalladium were added in turn, and the mixture was stirred at 100° C. for 1 hour under argon atmosphere. The reaction solution was purified by silica gel column chromatography to obtain 70 mg of the objective compound as colorless oil.

Workup

customThe reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-de9d88ae8d444e87947cbfd260957174
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673891B2

Reaction notes

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