Triethylamine → HCID 5328400, compound

HRID 1489595Notes

Reaction equation

HRID 1489595 reaction equation
ClC1C2SC3C=CC=CC=3C=2N=CN=1.[C:15]1([C@H:21]([NH:23][C:24]2[C:25]3[S:32][C:31]4[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=4[C:26]=3[N:27]=[CH:28][N:29]=2)[CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1([C@H](N)C)C=CC=CC=1.CCN(CC)CC>C(O)CC>[C:15]1([C@H:21]([NH:23][C:24]2[C:25]3[S:32][C:31]4[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=4[C:26]=3[N:27]=[CH:28][N:29]=2)[CH3:22])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6431891-Phenethylamine, (+)-HCID 86751418HCID 86751418, compound

Product 1

HCID 5328400HCID 5328400, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

4-([R]-1-Phenylethylamino)benzothieno[3,2-d]pyrimidine 4-Chlorobenzothieno[3,2-d]pyrimidine (110.1 mg, 0.5 mmol), [R]-1-phenylethylamine (74 mg, 0.6 mmol) and NEt3 (111 mg, 1.1 mmol) in stirred propanol (2 mL) are heated at reflux under N2 for 9 h. The mixture is allowed to cool, and is then purified by preparative tlc on silica, eluting once with 2% MeOH in CHCl3. The yellow solid is recrystallized from EtOH at 0° C. to give 4-([R]-1-phenylethylamino)benzothieno[3,2-d]pyrimidine, (75 mg, 49%) as pale yellow cubic crystals. 1H NMR (DMSO) δ8.53(1H, s), 8.30(1H, d, J=7.2 Hz), 8.15 (1H, d, J=8.2 Hz), 7.68 (1H, dt, Jd =1.2 Hz, Jt =7.5Hz), 7.58 (1H, dt, Jd =1 Hz, Jt =7.5 Hz), 7.44 (1H, dd, J=1, 8 Hz), 7.31 (2H, t, J=7.7 Hz), 7.21 (1 H, tt, J=1, 7.7 Hz), 5.58(1H, q, J =7 Hz), 1.58 (3H, d, J=7 Hz).

Workup

  1. temperatureat reflux under N2 for 9 h
  2. temperatureto cool
  3. customis then purified by preparative tlc on silica
  4. washeluting once with 2% MeOH in CHCl3
  5. customThe yellow solid is recrystallized from EtOH at 0° C.

Sources & evidence

ORD record
ord-c0201f8aab464724a90ec8bd133c19d6
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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