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1,2-Dichloroethane → 5-methyl-6-(4-phenylpiperazine-1-carbonyl)thieno[2,3-d]pyrimidin-4(3H)-one

HRID 1094714
Notes
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Reaction equation

HRID 1094714 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:12]([OH:14])=O.C(Cl)Cl.C(Cl)CCl.[C:22]1([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:12]([N:31]1[CH2:32][CH2:33][N:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:29][CH2:30]1)=[O:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6344DichloromethaneHCID 70961-PhenylpiperazineHCID 4058025-methyl-4-oxo-3H,4H-thieno[2,3-d]pyrimidine-6-carboxylic acid

Product 1

HCID 49910945-methyl-6-(4-phenylpiperazine-1-carbonyl)thieno[2,3-d]pyrimidin-4(3H)-oneYield 57%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid, (0.42 g, 2 mmol) in 1:1 DCM and DMF (10 mL) was added EDC (0.764 g, 4 mmol), DMAP (cat.) and 4-phenylpiperazine (0.324 g, 2 mmol). The reaction was stirred at RT overnight and DCM was removed. The resultant residue was partitioned between EtOAc (50 mL) and H2O (50 mL). The organic layer was dried over Na2SO4 and concentrated to provide 0.4 g 5-methyl-6-(4-phenylpiperazine-1-carbonyl)thieno[2,3-d]pyrimidin-4(3H)-one, (yield: 57%).

Workup

  1. customDCM was removed
  2. customThe resultant residue was partitioned between EtOAc (50 mL) and H2O (50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-96e3735af4de4f00a2f98c3faf893203
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08133998B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes