Triethylamine → 4-phenyl-3-(1-(thieno[2,3-d]pyrimidin-4-ylamino)ethyl)-1H-isochromen-1-one

HRID 634482Notes

Reaction equation

HRID 634482 reaction equation
Cl.[NH2:2][CH:3]([C:5]1[O:6][C:7](=[O:21])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:4].Cl[C:23]1[C:24]2[CH:31]=[CH:30][S:29][C:25]=2[N:26]=[CH:27][N:28]=1.C(N(CC)CC)C>CC(O)(C)C>[C:15]1([C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:21])[O:6][C:5]=2[CH:3]([NH:2][C:23]2[C:24]3[CH:31]=[CH:30][S:29][C:25]=3[N:26]=[CH:27][N:28]=2)[CH3:4])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 7366184-Chlorothieno[2,3-d]pyrimidine2×HCID 1181314633-(1-aminoethyl)-4-phenyl-1H-isochromen-1-one hydrochloride2×

Product 1

HCID 1181312864-phenyl-3-(1-(thieno[2,3-d]pyrimidin-4-ylamino)ethyl)-1H-isochromen-1-oneYield 47%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

3-(1-aminoethyl)-4-phenyl-1H-isochromen-1-one hydrochloride (intermediate E2 50 mg, 0.166 mmol), 4-chlorothieno[2,3-d]pyrimidine (36.8 mg, 0.215 mmol), triethylamine (0.046 ml, 0.331 mmol) were reacted in 2-methylpropan-2-ol (1 ml) at 80° C. for 6 hrs and at 50° C. for 60 hrs. 4-Chlorothieno[2,3-d]pyrimidine (5.7 mg, 0.033 mmol), triethylamine (0.09 ml, 0.066 mmol) were added and the mixture reacted at 90° C. for 4 hrs. The crude was purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) to give the title compound (31 mg, 47%).

Workup

  1. customthe mixture reacted at 90° C. for 4 hrs
  2. customThe crude was purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%)

Sources & evidence

ORD record
ord-53571eb17c6a41509f0ff9199ef91503
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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