1-((2-(2-aminopyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)-N-methylpiperidine-4-carboxamide → 5-(6-((1-Methylpiperidin-4-yl-n-methylamino)methyl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

HRID 390906Notes

Reaction equation

HRID 390906 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]([CH3:20])[CH:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)=[C:8]([CH3:21])[C:6]=2[N:7]=1.[NH2:28][C:29]1[N:34]=[CH:33][C:32](C2N=C(N3CCOCC3)C3SC(CN4CCC(C(NC)=O)CC4)=CC=3N=2)=[CH:31][N:30]=1>>[CH3:19][N:16]1[CH2:17][CH2:18][CH:13]([N:12]([CH2:11][C:9]2[S:10][C:5]3[C:4]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[N:3][C:2]([C:32]4[CH:31]=[N:30][C:29]([NH2:28])=[N:34][CH:33]=4)=[N:7][C:6]=3[C:8]=2[CH3:21])[CH3:20])[CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 582338521-((2-(2-aminopyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)-N-methylpiperidine-4-carboxamideHCID 86623525N-((2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)-N,1-dimethylpiperidin-4-amine

Product 1

HCID 582340715-(6-((1-Methylpiperidin-4-yl-n-methylamino)methyl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amineYield 5%

Procedure

N-((2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)-N,1-dimethylpiperidin-4-amine following Example 115 (0.23 mmol) was reacted using General Procedure A: Suzuki Coupling to give 190 (TFA salt) in a 5% yield after reverse-phase HPLC purification. MS (Q1) 469 (M)+.

Sources & evidence

ORD record
ord-1a9cedec07cf452db26fe2591beaa7db
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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