N,N-Dimethylglycine → 2-dimethylamino-1-{4-[4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenylamino]-5,8-dihydro-6H-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-7-yl}-ethanone

HRID 450575Notes

Reaction equation

HRID 450575 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:34][N:35]([CH3:40])[CH2:36][C:37](O)=[O:38].[F:41][C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:49]2[C:50]3[C:57]4[CH2:58][CH2:59][NH:60][CH2:61][C:56]=4[S:55][C:51]=3[N:52]=[CH:53][N:54]=2)=[C:44]([O:62][CH:63]2[CH2:68][CH2:67][O:66][CH2:65][CH2:64]2)[CH:43]=1>CN(C=O)C.O>[CH3:34][N:35]([CH3:40])[CH2:36][C:37]([N:60]1[CH2:59][CH2:58][C:57]2[C:50]3[C:49]([NH:48][C:45]4[CH:46]=[CH:47][C:42]([F:41])=[CH:43][C:44]=4[O:62][CH:63]4[CH2:68][CH2:67][O:66][CH2:65][CH2:64]4)=[N:54][CH:53]=[N:52][C:51]=3[S:55][C:56]=2[CH2:61]1)=[O:38]

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 46182217[4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenyl]-(5,6,7,8-tetrahydro-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-yl)-amine

Product 1

HCID 461822182-dimethylamino-1-{4-[4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenylamino]-5,8-dihydro-6H-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-7-yl}-ethanoneYield 40.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (0.285 g, 0.75 mmol) was added into a stirred solution of Hünig's base (0.13 mL, 0.75 mmol) and N,N-dimethylglycine (0.077 g, 0.75 mmol) in DMF (1.0 mL) and the mixture stirred for 20 minutes at ambient temperature. [4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenyl]-(5,6,7,8-tetrahydro-pyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-yl)-amine (0.10 g, 0.25 mmol) was added and the mixture stirred for 18 hours. Water (5 mL) was added and the mixture stirred for 20 minutes. The precipitated solid was collect by filtration, washed with water (10 mL), diethyl ether (10 mL), and dried under vacuum to give a colourless solid (0.049 g, 40%).

Workup

  1. stirringthe mixture stirred for 18 hours
  2. stirringthe mixture stirred for 20 minutes
  3. filtrationThe precipitated solid was collect by filtration
  4. washwashed with water (10 mL), diethyl ether (10 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-27991f20f2bd4009be2b3a54382c10df
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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