Hydrochloric Acid → (3-Methyl-1H-indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amine

HRID 2297820Notes

Reaction equation

HRID 2297820 reaction equation
[C:1]1([C:7]2[S:15][C:14]3[C:13]([NH:16][C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[NH:22][CH:21]=[C:20]5[CH:26]=O)=[N:12][CH:11]=[N:10][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].[Cl-].[NH4+].Cl>C(Cl)Cl.[I-].[Zn+2].[I-]>[CH3:26][C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([NH:16][C:13]3[C:14]4[S:15][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:8][C:9]=4[N:10]=[CH:11][N:12]=3)[CH:18]=2)[NH:22][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 5003444Sodium cyanoborohydrideHCID 183827505-(6-Phenyl-thieno[3,2-d]pyrimidin-4-ylamino)-1H-indole-3-carbaldehyde

Product 1

HCID 18382736(3-Methyl-1H-indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amineYield 31%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-(6-phenyl-thieno[3,2-d]pyrimidin-4-ylamino)-1H-indole-3-carbaldehyde (75 mg, 0.203 mmol) in 5 mL of methylene chloride was added zinc iodide (97 mg, 0.303) and sodium cyanoborohydride (97 mg, 1.522 mmol). The reaction mixture was refluxed for 24 hours and then cooled to ambient temperature and poured into an ice-cooled mixture of saturated ammonium chloride. The solution was then neutralized with 6N HCl and extracted with ethyl acetate (3×, 50 mL). The organic extracts were dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed using a Biotage Autoflash 40 system and 1% MeOH/CH2Cl2 to produce the title compound (22 mg, 31% yield). RP18-HPLC RT: 6.071 minutes; API MS: 357.10 (M+1); MP: 221-223° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate (3×, 50 mL)
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed

Sources & evidence

ORD record
ord-722fe741585145149bbf6762e1055637
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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