Acetic Acid → 2-[4-(4-hydroxyphenyl)piperazin-1-yl]-6,7-dihydro-1H-thieno[3,2-d]pyrimidin-4-one

HRID 1805990Notes

Reaction equation

HRID 1805990 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:14]([OH:17])(=O)[CH3:15].Cl[C:19]1[N:20]=C(NC2C=C(C=CC=2)C(O)=O)C2[S:27][CH2:26][CH2:25][C:23]=2[N:24]=1>O>[OH:13][C:10]1[CH:9]=[CH:8][C:7]([N:1]2[CH2:2][CH2:3][N:4]([C:19]3[N:20]=[C:14]([OH:17])[C:15]4[S:27][CH2:26][CH2:25][C:23]=4[N:24]=3)[CH2:5][CH2:6]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 92467p-(1-Piperazinyl)phenolHCID 576001073-(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)benzoic acid

Product 1

HCID 1785162312-[4-(4-hydroxyphenyl)piperazin-1-yl]-6,7-dihydro-1H-thieno[3,2-d]pyrimidin-4-oneYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

1.70 g (9.54 mmol) of 4-piperazin-1-ylphenol is placed in 0.55 mL (9.62 mmol) of glacial acetic acid and heated to 180° C. in the heating block. 0.800 g (3.73 mmol) of 2-ethylsulfanyl-6,7-dihydrothieno[3,2-d]pyrimidin-4-ol (I) is added, then the mixture is left to stand for 1.5 hours at 180° C. and 16 hours at ambient temperature. Then the reaction mixture is combined with water and treated in the ultrasound bath. The precipitate is suction filtered, washed, and dried. 1.1 g of product II is obtained as a powder.

Workup

  1. waitthe mixture is left
  2. additiontreated in the ultrasound bath
  3. filtrationfiltered
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-61a33495effe4e8ab5e5ae72bbee60b4
Source dataset
uspto-grants-2013_01
Patent number
US08354531B2

Reaction notes

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