Potassium Carbonate → 2-Chloro-4-(4-methyl-piperazin-1-yl)-thieno[3,2-d]pyrimidine

HRID 1422982Notes

Reaction equation

HRID 1422982 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CCO>[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 866287402-Chloro-4-(4-methyl-piperazin-1-yl)-thieno[3,2-d]pyrimidineYield 85.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichloro-thieno[3,2-d]pyrimidine (0.20 g, 1.0 mmol) in EtOH (3.2 mL) was added K2CO3 (0.31 g, 2.2 mmol) followed by N-methylpiperazine (0.13 mL, 1.2 mmol). After stirring at rt for 12 h, the mixture was filtered to afford 0.23 g of the desired product. MS: 269.0. 1H NMR (400 MHz, CD3OD) 8 ppm 8.06 (d, J=5.6 Hz, 1H), 7.27 (d, J=5.6 Hz, 1H), 4.05-4.00 (m, 4H), 2.62-2.56 (m, 4H), 2.36 (s, 3H).

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-1a0974cc28eb439e8fe2c669d9ffcaf5
Source dataset
uspto-grants-2015_01
Patent number
US08927555B2

Reaction notes

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