1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-Ethoxy-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-amine

HRID 1507877Notes

Reaction equation

[NH2:1][C:2]1[NH:3][C:4](=[O:18])[C:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[S:8][C:6]=2[N:7]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:30]2C=CC=C[C:29]=2N=N1.C1CCN2C(=NCCC2)CC1.[O-]CC.[Na+]>CCO>[CH2:29]([O:18][C:4]1[C:5]2[CH:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[S:8][C:6]=2[N:7]=[C:2]([NH2:1])[N:3]=1)[CH3:30]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one (50 mg, 0.19 mmol) and BOP (110 mg, 0.25 mmol) in EtOH (1 ml) was added DBU (43 μl, 0.29 mmol). The resulting mixture was heated at 60° C. for 4 hours. After cooling down to room temperature, sodium ethoxide (26 mg, 0.38 mmol) was added. The mixture was again heated at 60° C. overnight. The solvents were removed under reduced pressure and the crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 60:1) yielding the title compound as a white solid (30 mg, 54%).

Workup

temperatureAfter cooling down to room temperature
temperatureThe mixture was again heated at 60° C. overnight
customThe solvents were removed under reduced pressure
customthe crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 60:1)

Sources & evidence

ORD record: ord-4d0ead970e6f453c97950d2c30588ac0
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221822B2

Reaction notes

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