2-Methoxyethanol → tert-Butyl 4-{[(1R)-1-phenylethyl]amino}-5,8-dihydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(6H)-carboxylate

HRID 38519Notes

Reaction equation

Cl[C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.C([N:24]([CH2:27][CH3:28])CC)C.CO[CH2:31][CH2:32]O>C(OCC)(=O)C>[C:32]1([C@H:27]([NH:24][C:2]2[C:3]3[C:10]4[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:9]=4[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH3:28])[CH:31]=[CH:9][CH:10]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

tert-Butyl 4-chloro-5,8-dihydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine-7(6H)-carboxylate from Example 11A (500 mg, 1.54 mmol) was dissolved in 2-methoxyethanol (5 mL), and (R)-methylbenzylamine (223 mg, 1.84 mmol) and triethylamine (621 mg, 6.14 mmol) were added. The mixture was heated to 100° C. for 2 h, then diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1) to yield 474 mg (75%) of the title compound.

Workup

washwashed with water
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent was removed in vacuo
customThe crude product was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1)

Sources & evidence

ORD record: ord-10f1f9b0d8c64aae9baab17efca60ad2
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524722B2

Reaction notes

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