1-((2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)piperidin-4-ol → 1-((2-(2-(Methylamino)pyrimidin-5-yl)-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)piperidin-4-ol

HRID 391096Notes

Reaction equation

HRID 391096 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[CH:10]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]3)[S:8][C:6]=2[N:7]=1.[CH3:25][N:26]([C:34]1[N:39]=[CH:38][C:37](B2OC(C)(C)C(C)(C)O2)=[CH:36][N:35]=1)C(=O)OC(C)(C)C>>[CH3:25][NH:26][C:34]1[N:39]=[CH:38][C:37]([C:2]2[N:3]=[C:4]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:5]3[CH:10]=[C:9]([CH2:11][N:12]4[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]4)[S:8][C:6]=3[N:7]=2)=[CH:36][N:35]=1

Participants

3

Reactant 2

HCID 582339121-((2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)piperidin-4-olHCID 58234002Tert-butyl methyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate

Product 1

HCID 582339531-((2-(2-(Methylamino)pyrimidin-5-yl)-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)piperidin-4-olYield 24%

Procedure

1-((2-chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)piperidin-4-ol (187 mg, 0.5 mmol) was utilized in a Suzuki coupling with tert-butyl methyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate (238 mg, 0.7 mmol) according to General Procedure Suzuki to provide 381 (53 mg) after reverse phase HPLC purification. MS (Q1) 442 (M)+

Sources & evidence

ORD record
ord-35996507d61c4109aae3671516815988
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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