Aniline → HCID 11956657, compound

HRID 2240108Notes

Reaction equation

HRID 2240108 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.[C:23]1([NH2:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[C:23]1([NH:29][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)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 866162644-Chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine

Product 1

HCID 11956657HCID 11956657, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.300 g (0.90 mmol) of 4-chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine (V) and 3 mL of phenylamine are combined, then reacted for 0.3 hours at 130° C. in the microwave. Then the reaction mixture is combined with water and extracted with ethyl acetate. The organic phase is dried and evaporated to dryness. The residue is triturated with diethyl ether and suction filtered. 0.18 g of product I (51%) is obtained (m.p. 174° C.-175° C.). 1H-NMR (400 MHz, DMSO): 8.59 (1H, s); 7.63 (2H, d); 7.31 (2H, t); 7.22 (2H, t); 7.03 (1H, t); 6.99 (2H, d); 6.80 (1H, t); 3.83-3.73 (4H, m); 3.31 (2H, t); 3.23 (4H, m); 3.12 (2H, t).

Workup

  1. customreacted for 0.3 hours at 130° C. in the microwave
  2. extractionextracted with ethyl acetate
  3. customThe organic phase is dried
  4. customevaporated to dryness
  5. customThe residue is triturated with diethyl ether and suction
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b4524cc4460b4c35bbe6925b2229ae48
Source dataset
uspto-grants-2010_05
Patent number
US07723341B2

Reaction notes

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