5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine → 5-Fluoro-N-(2-fluoro-4-(morpholinomethyl)phenyl)-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine

HRID 18

反应方程式

HRID 18 反应方程式
Cc1ncc(-c2nc(N)ncc2F)n1C1CCOCC1.Fc1cc(CN2CCOCC2)ccc1Br>C1CCCC1.CC(C1CCCC1P(C1CCCCC1)C1CCCCC1)P(C(C)(C)C)C(C)(C)C.CCC(C)(C)[O-].Cc1ccccc1.[Fe].[Na+].[Pd]>Cc1ncc(-c2nc(Nc3ccc(CN4CCOCC4)cc3F)ncc2F)n1C1CCOCC1

参与物

7

反应物 2

HCID 166654985-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amineHCID 534178184-(4-Bromo-3-fluorobenzyl)morpholine

产物 1

HCID 497820135-Fluoro-N-(2-fluoro-4-(morpholinomethyl)phenyl)-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine收率 79%

试剂、催化剂与溶剂 4

HCID 2733478叔戊醇钠试剂HCID 23938钯催化剂HCID 144543273(R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene, 1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-, (2R)-催化剂HCID 1140甲苯溶剂

反应条件

温度
110 °C

实验过程

The aim of the reaction is test/optimization: 5-fluoro-4-(2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)pyrimidin-2-amine (100 mg, 0.36 mmol), 4-(4-bromo-3-fluorobenzyl)morpholine (109 mg, 0.40 mmol), Palladium, 10% On Charcoal (115 mg, 0.11 mmol), (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (91 mg, 0.16 mmol) and Sodium tert-pentoxide (79 mg, 0.72 mmol) were dissolved in toluene (1.5 mL) and heated to 110 °C under argon. The reaction was monitorred by HPLC. After 16 h 79 % conversion was achieved. The reaction was stopped and the mixture was discarded.

来源与证据

ORD记录
ord-2c710cb7fbbd4d70b492cf6ab2e6cbf5
来源数据集
750 AstraZeneca ELN dataset
原始链接
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