4-Chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine → HCID 11956655, compound

HRID 1805974Notes

Reaction equation

HRID 1805974 reaction equation
Cl[C:2]1[C:3]2[S:22][CH2:21][CH2:20][C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[N:7]=1>C1(N)CCCCC1>[CH:14]1([NH:11][C:2]2[C:3]3[S:22][CH2:21][CH2:20][C:4]=3[N:5]=[C:6]([N:8]3[CH2:13][CH2:12][N:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:10][CH2:9]3)[N:7]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

3

Reactant 1

HCID 866162644-Chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine

Product 1

HCID 11956655HCID 11956655, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 7965CyclohexylamineSolvent

Procedure

0.300 g (0.90 mmol) of 4-chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine (V) is placed in 4 mL of cyclohexylamine, then reacted for 0.1 hours at 130° C. in the microwave. Then the reaction mixture is concentrated by evaporation, the residue is stirred with water and suction filtered. 0.120 g of product I (34%) is obtained as a powder. 1H NMR (400 MHz, DMSO): 7.22 (2H, t); 6.97 (2H, d); 6.79 (1H, t); 6.08 (1H, d); 3.93-3.81 (1H, m); 3.80-3.69 (4H, m); 3.22 (2H, t); 3.18-3.11 (4H, m); 2.98 (2H, t); 1.92-1.79 (2H, m); 1.79-1.66 (2H, m); 1.66-1.55 (1H, m); 1.37-1.21 (4H, m); 1.18-1.04 (1H, m).

Workup

  1. customreacted for 0.1 hours at 130° C. in the microwave
  2. concentrationThen the reaction mixture is concentrated by evaporation
  3. filtrationfiltered

Sources & evidence

ORD record
ord-a9c65e5a0adf48c7bbe793fb22abe0c9
Source dataset
uspto-grants-2013_01
Patent number
US08354531B2

Reaction notes

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