Acetic Anhydride → N-(5-(4-morpholino-6-((4-(2-(tetrahydro-2H-pyran-2-yloxy)acetyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyridin-2-yl)acetamide

HRID 390899Notes

Reaction equation

HRID 390899 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:11]3[S:16][C:15]([CH2:17][N:18]4[CH2:23][CH2:22][N:21]([C:24](=[O:33])[CH2:25][O:26][CH:27]5[CH2:32][CH2:31][CH2:30][CH2:29][O:28]5)[CH2:20][CH2:19]4)=[CH:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[C:40](OC(=O)C)(=[O:42])[CH3:41]>N1C=CC=CC=1>[O:37]1[CH2:36][CH2:35][N:34]([C:10]2[C:11]3[S:16][C:15]([CH2:17][N:18]4[CH2:19][CH2:20][N:21]([C:24](=[O:33])[CH2:25][O:26][CH:27]5[CH2:32][CH2:31][CH2:30][CH2:29][O:28]5)[CH2:22][CH2:23]4)=[CH:14][C:12]=3[N:13]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:40](=[O:42])[CH3:41])=[N:7][CH:6]=3)[N:9]=2)[CH2:39][CH2:38]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 669339581-(4-((2-(6-Aminopyridin-3-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-(tetrahydro-2H-pyran-2-yloxy)ethanone

Product 1

HCID 66934144N-(5-(4-morpholino-6-((4-(2-(tetrahydro-2H-pyran-2-yloxy)acetyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyridin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(4-((2-(6-Aminopyridin-3-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-(tetrahydro-2H-pyran-2-yloxy)ethanone (110 mg) was reacted with 80 μL acetic anhydride in 500 μL pyridine overnight at 40° C. to give N-(5-(4-morpholino-6-((4-(2-(tetrahydro-2H-pyran-2-yloxy)acetyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyridin-2-yl)acetamide. This intermediate was subjected to Procedure D to remove the THP protecting group and give 6.3 mg of 184 after purification. MS (Q1) 512.3 (M)+.

Sources & evidence

ORD record
ord-20b16c9b41634b169c73786d29af9797
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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