HCID 53236148, compound → HCID 53239539, compound

HRID 1485509Notes

Reaction equation

HRID 1485509 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10]2[N:11]=[C:12]([NH:21][C@@H:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)C)[C:13]3[S:18][CH:17]=[C:16]([CH:19]=[CH2:20])[C:14]=3[N:15]=2)[CH2:3][CH2:2]1.[H][H]>CO.[Ni]>[CH2:22]([NH:21][C:12]1[C:13]2[S:18][CH:17]=[C:16]([CH2:19][CH3:20])[C:14]=2[N:15]=[C:10]([NH:9][CH2:8][CH2:7][N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[N:11]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 53236148HCID 53236148, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53239539HCID 53239539, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney Ni was added to (R)—N2-(2-Morpholinoethyl)-N4-(1-phenylethyl)-7-vinylthieno[3,2-d]pyrimidin-2,4-diamine (10 mg, 0.025 mmol) in methanol (1 mL), and the mixture was stirred at room temperature for 24 hours under a pressure of a balloon filled with hydrogen gas. Filtration of the reaction mixture with celite followed by washing with methanol and concentration yielded the target compound (9 mg, 89% yield).

Workup

  1. filtrationFiltration of the reaction mixture with celite
  2. washby washing with methanol and concentration

Sources & evidence

ORD record
ord-c0505ef7320c4fa091a009f925fd478d
Source dataset
uspto-grants-2016_08
Patent number
US09422307B2

Reaction notes

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