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

HRID 1365411Notes

Reaction equation

HRID 1365411 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[CH:10]=[C:9]([CH2:11][N:12]3[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13]3)[S:8][C:6]=2[N:7]=1.[CH3:24][N:25]([C:33]1[N:38]=[CH:37][C:36](B2OC(C)(C)C(C)(C)O2)=[CH:35][N:34]=1)C(=O)OC(C)(C)C>>[CH3:24][NH:25][C:33]1[N:38]=[CH:37][C:36]([C:2]2[N:3]=[C:4]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:5]3[CH:10]=[C:9]([CH2:11][N:12]4[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13]4)[S:8][C:6]=3[N:7]=2)=[CH:35][N:34]=1

Participants

3

Reactant 2

HCID 582339241-((2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)pyrrolidin-3-olHCID 58234002Tert-butyl methyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate

Product 1

HCID 582339481-((2-(2-(Methylamino)pyrimidin-5-yl)-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)pyrrolidin-3-olYield 29%

Procedure

1-((2-chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)pyrrolidin-3-ol (235 mg, 0.67 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 (311 mg, 0.93 mmol) according to General Procedure Suzuki to provide 380 (83 mg) after reverse phase HPLC purification. MS (Q1) 428 (M)+

Sources & evidence

ORD record
ord-9683dfc20bb646b688089839d60237b2
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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