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3,4,5-Trimethoxyaniline → 2-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide

HRID 1773624
Notes
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Reaction equation

HRID 1773624 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]([OH:13])=O)[C:6]=2[N:7]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[NH2:19].C(N(CC)C(C)C)(C)C.C1CN(C(ON2N=NC3C2=CC=CC=3)=[N+]2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.O.CN(C)C=O>[CH3:26][O:25][C:21]1[CH:20]=[C:18]([NH:19][C:11]([C:8]2[C:6]3[N:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=3[S:10][CH:9]=2)=[O:13])[CH:17]=[C:16]([O:15][CH3:14])[C:22]=1[O:23][CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 322853,4,5-TrimethoxyanilineHCID 81531DiisopropylethylamineHCID 13685355O-(Benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)uronium HexafluorophosphateHCID 580563052-Chlorothieno[3,2-D]pyrimidine-7-carboxylic acid

Product 1

HCID 866613792-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.050 g (0.233 mmole) 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid, 0.0854 g (0.466 mmole) of 3,4,5-trimethoxyaniline, 0.122 mL (0.699 mmole) of N,N-diisopropylethylamine and 1.55 mL of dimethylformamide was added 0.111 g (0.256 mmole) of O-(benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uronium hexafluorophosphate. The mixture was stirred at room temperature for 2 hours. Water and dichloromethane were added. The aqueous layer was washed three times with dichloromethane. The combined organic layer was washed with aqueous sodium carbonate, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dried in high vacuum to give 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide as a yellow solid

Workup

  1. washThe aqueous layer was washed three times with dichloromethane
  2. washThe combined organic layer was washed with aqueous sodium carbonate, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was dried in high vacuum

Sources & evidence

ORD record
ord-24bd8791008c4730bbb7c2c35c369197
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09255110B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes