4-Chloro-5-methylthieno[2,3-d]pyrimidine → 4-[2-Methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]-5-methylthieno[2,3-d]pyrimidine

HRID 1837471Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].Cl[C:25]1[C:26]2[C:33]([CH3:34])=[CH:32][S:31][C:27]=2[N:28]=[CH:29][N:30]=1>C(O)(C)C>[CH3:8][C:7]1[CH:6]=[CH:5][C:4]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[CH:13]=2)=[O:11])=[CH:3][C:2]=1[NH:1][C:25]1[C:26]2[C:33]([CH3:34])=[CH:32][S:31][C:27]=2[N:28]=[CH:29][N:30]=1

Participants

Conditions

Temperature: 88 °C

Procedure

N-(3-amino-4-methylphenyl)-2-morpholinopyridine-4-carboxamide (0.056 g), 4-chloro-5-methylthieno[2,3-d]pyrimidine (Maybridge Chemical Company, Trevillet, Tintagel, Cornwall, PL34 0HW, GB; 0.037 g) and isopropanol (2 ml) and the reaction mixture was stirred and heated to 88° C. for 18 hours. The reaction mixture was cooled to ambient temperature and the precipitate was isolated and washed in turn with isohexane and diethyl ether. There was thus obtained the title compound (0.021 g); Mass: M+H+ 461.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
customthe precipitate was isolated
washwashed in turn with isohexane and diethyl ether

Sources & evidence

ORD record: ord-9ee3689c8f5440d0a2f65b0cd3e41f3d
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06784174B1

Reaction notes

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