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Dimethylformamide dimethyl acetal → 6-(4-Chlorophenyl)-3-[3-methoxy-4-(2-methyl-2-pyrrolidin-1-ylpropoxy)phenyl]thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1181354
Notes
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Reaction equation

HRID 1181354 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([O:16]C)=O.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]([CH3:36])([N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)[CH3:30])[NH2:23].[CH3:37]N(C(OC)OC)C>C(O)C>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:14](=[O:16])[N:23]([C:22]4[CH:24]=[CH:25][C:26]([O:27][CH2:28][C:29]([CH3:36])([N:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[CH3:30])=[C:20]([O:19][CH3:18])[CH:21]=4)[CH:37]=[N:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 2777492Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylateHCID 589808333-Methoxy-4-(2-methyl-2-pyrrolidin-1-ylpropoxy)aniline

Product 1

HCID 589808306-(4-Chlorophenyl)-3-[3-methoxy-4-(2-methyl-2-pyrrolidin-1-ylpropoxy)phenyl]thieno[3,2-d]pyrimidin-4(3H)-oneYield 8%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
110 °C

Procedure

Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate (0.639 g, 0.2390 mmol) was taken up in DMF-DMA (3 mL) and heated to 110° C. The reaction was stirred for 3 h and then concentrated. 3-Methoxy-4-(2-methyl-2-pyrrolidin-1-ylpropoxy)aniline (0.0631 g, 0.2390 mmol) in absolute ethanol (3 mL) was added to the residue and the mixture was then concentrated. Fresh absolute ethanol (1 mL) was added and the reaction heated to reflux. The reaction was stirred for 18 h and then cooled to RT and the precipitate was collected to give 0.010 g (0.020 mmol, 8%) of the product as a white solid. 1H NMR (CDCl3) δ 8.15 (s, 1H), 7.65 (d, 2H, J=8.3 Hz), 7.53 (s, 1H), 7.44 (d, 2H, J=8.5 Hz), 7.18 (d, 1H, J=8.3 Hz), 6.96 (s, 1H), 6.88 (d, 1H, J=8.3 Hz), 3.83 (s, 3H, 2.77 (s, 2H), 2.72 (bs, 4H), 1.78 (bs, 4H), 1.36 (s, 6H).

Workup

  1. concentrationconcentrated
  2. concentrationthe mixture was then concentrated
  3. additionFresh absolute ethanol (1 mL) was added
  4. temperaturethe reaction heated to reflux
  5. stirringThe reaction was stirred for 18 h
  6. temperaturecooled to RT
  7. customthe precipitate was collected

Sources & evidence

ORD record
ord-f1d72c610b6749edae904cb1b00aed08
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07285557B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes