Ammonia → 5-(2-Phenylquinolin-7-yl)-thieno[2,3-d]pyrimidin-4-ylamine

HRID 230238Notes

Reaction equation

HRID 230238 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)=[N:18]4)=[CH:13][CH:12]=3)=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:27]>CC(O)C>[C:21]1([C:17]2[CH:16]=[CH:15][C:14]3[C:19](=[CH:20][C:11]([C:10]4[C:3]5[C:2]([NH2:27])=[N:7][CH:6]=[N:5][C:4]=5[S:8][CH:9]=4)=[CH:12][CH:13]=3)[N:18]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 577623927-(4-Chlorothieno[2,3-d]pyrimidin-5-yl)-2-phenylquinoline2×

Product 1

HCID 160687065-(2-Phenylquinolin-7-yl)-thieno[2,3-d]pyrimidin-4-ylamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
-78 °C

Procedure

From 7-(4-chlorothieno[2,3-d]pyrimidin-5-yl)-2-phenylquinoline: Gaseous NH3 was bubbled into a iPrOH (1 ml) solution of 7-(4-chlorothieno[2,3-d]pyrimidin-5-yl)-2-phenylquinoline (56 mg, max. 0.084 mmol) in a sealable tube, cooled to −78° C. in a dry ice/acetone bath, for 15 min. The sealed tube was equipped with a Teflon washer, sealed and heated at 110° C. for 8 h. After that time, the excess NH3 and the solvent were evaporated. The remaining material was purified by HPLC to give the title compound as an off-white solid.

Workup

  1. customsealed
  2. temperatureheated at 110° C. for 8 h
  3. customAfter that time, the excess NH3 and the solvent were evaporated
  4. customThe remaining material was purified by HPLC

Sources & evidence

ORD record
ord-f1e026bbdb8d4ba880db627c68425f97
Source dataset
uspto-grants-2009_07
Patent number
US07566721B2

Reaction notes

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