N,N-Dimethyl-1,3-propanediamine → 3-(Dimethylamino)propyl-4-(4-fluoro-2-((tetrahydro-2-H-pyran-4-yl)methoxy)phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxamide

HRID 532291Notes

Reaction equation

HRID 532291 reaction equation
C[N:2](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](O)=[O:44])[S:39][C:35]=3[N:36]=[CH:37][N:38]=2)=[C:28]([O:46][CH2:47][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][N:64]([CH3:69])[CH2:65][CH2:66][CH2:67]N>CN(C=O)C.CCOC(C)=O>[CH3:63][N:64]([CH3:69])[CH2:65][CH2:66][CH2:67][C:37]1[N:38]=[C:33]([NH:32][C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][C:28]=2[O:46][CH2:47][CH:48]2[CH2:49][CH2:50][O:51][CH2:52][CH2:53]2)[C:34]2[C:41]([CH3:42])=[C:40]([C:43]([NH2:2])=[O:44])[S:39][C:35]=2[N:36]=1

Participants

7

Reactant 4

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584133504-(4-Fluoro-2-((tetrahydro-2-H-pyran-4-yl)methoxy)phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid

Product 1

HCID 1317319193-(Dimethylamino)propyl-4-(4-fluoro-2-((tetrahydro-2-H-pyran-4-yl)methoxy)phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HATU (36 mg) was added to a solution of 4-(4-fluoro-2-((tetrahydro-2-H-pyran-4-yl)methoxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylic acid (36 mg) and DIPEA (17 μl) in DMF (1 ml). The reaction mixture was stirred for 40 min at room temperature. Then 3-(dimethylamino)propylamine (49 μl) was added. The reaction mixture was stirred at room temparture overnight. It was diluted with EtOAc and washed with water and brine. The organic phase was concentrated in vacuo. The residue was suspended in Et2O and filtered and dried.

Workup

  1. stirringThe reaction mixture was stirred at room temparture overnight
  2. washwashed with water and brine
  3. concentrationThe organic phase was concentrated in vacuo
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-fc71c7c04ed14c118276658fc99705b2
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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