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2-Methoxyethylamine → 4-(4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-N-(2-methoxyethyl)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide

HRID 450535
Notes
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Reaction equation

HRID 450535 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]2[C:34]3[C:41]([CH3:42])=[C:40]([C:43](OC)=[O:44])[S:39][C:35]=3[N:36]=[CH:37][N:38]=2)=[C:28]([O:47][CH:48]2[CH2:53][CH2:52][O:51][CH2:50][CH2:49]2)[CH:27]=1.CCN(C(C)C)C(C)C.[CH3:63][O:64][CH2:65][CH2:66][NH2:67]>CN(C=O)C>[F:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]2[C:34]3[C:41]([CH3:42])=[C:40]([C:43]([NH:67][CH2:66][CH2:65][O:64][CH3:63])=[O:44])[S:39][C:35]=3[N:36]=[CH:37][N:38]=2)=[C:28]([O:47][CH:48]2[CH2:49][CH2:50][O:51][CH2:52][CH2:53]2)[CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 461820444-[4-Fluoro-2-(tetrahydro-pyran-4-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methylester

Product 1

HCID 46182042
4-(4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-N-(2-methoxyethyl)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide
Yield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

HATU (0.052 g, 0.138 mmol) was added into a mixture of methyl 4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (0.050 g, 0.125 mmol) and Hünig's base (22 μL, 0.125 mmol) in DMF (2.0 mL) at 0° C. The reaction mixture was stirred at 0° C. for 0.5 hours. 2-Methoxyethylamine (54.3 μL, 0.625 mmol) was added and the coolant removed. The reaction mixture was stirred at ambient temperature overnight. The product was purified by reverse phase preparative HPLC to yield white solid (0.029 g, 50%)

Workup

  1. customthe coolant removed
  2. stirringThe reaction mixture was stirred at ambient temperature overnight
  3. customThe product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-960802d9ccd848949415e3207e830ff3
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486953B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes