N,N-Dimethyl-1,3-propanediamine → N-(3-(Dimethylamino)propyl)-4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl-amino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide

HRID 450536Notes

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]([O:45]C)=O)[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][N:64]([CH3:69])[CH2:65][CH2:66][CH2:67][NH2:68]>CN(C=O)C>[CH3:63][N:64]([CH3:69])[CH2:65][CH2:66][CH2:67][NH:68][C:43]([C:40]1[S:39][C:35]2[N:36]=[CH:37][N:38]=[C:33]([NH:32][C:29]3[CH:30]=[CH:31][C:26]([F:25])=[CH:27][C:28]=3[O:47][CH:48]3[CH2:49][CH2:50][O:51][CH2:52][CH2:53]3)[C:34]=2[C:41]=1[CH3:42])=[O:45]

Participants

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. 3-Dimethylamino-1-propylamine (69 μL, 0.625 mmol) was added and the coolant removed. The reaction mixture was stirred at ambient temperature overnight. The product was recrystallised from DMSO to yield off-white solid (0.031 g, 51%).

Workup

customthe coolant removed
stirringThe reaction mixture was stirred at ambient temperature overnight
customThe product was recrystallised from DMSO

Sources & evidence

ORD record: ord-a8a25af9dbd8457b8191db1cabaac1e3
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486953B2

Reaction notes

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