1-Methyl-4-(methylamino)piperidine → 5-Chloro-N-methyl-N-(1-methylpiperidin-4-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-amine

HRID 1365831Notes

Reaction equation

HRID 1365831 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9](S(C)(=O)=O)=[N:8][C:6]=2[N:7]=1.[CH3:21][N:22]1[CH2:27][CH2:26][CH:25]([NH:28][CH3:29])[CH2:24][CH2:23]1>C(N(CC)CC)C>[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9]([N:28]([CH3:29])[CH:25]3[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]3)=[N:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 5663231-Methyl-4-(methylamino)piperidineHCID 576854065-Chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine

Product 1

HCID 866300855-Chloro-N-methyl-N-(1-methylpiperidin-4-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Alternatively, 5-chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine was reacted with 1-methyl-4-(methylamino)piperidine, without triethylamine, via General Procedure C, to give crude 5-chloro-N-methyl-N-(1-methylpiperidin-4-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-amine, which was then reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine via General Procedure C again to give 144 after purification by silica gel chromatography. MS (Q1) 441 (M+)

Sources & evidence

ORD record
ord-ba230d5c5e3e4a27a5b49adf0a9908d4
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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