Sodium cyanoborohydride → [(2,5-Diaza-bicyclo[2.2.1]hept-2-yl)-ethyl]-(5,6-diphenyl-furo[2,3-d]pyrimidin-4-yl)-amine

HRID 502659Notes

Reaction equation

HRID 502659 reaction equation
C(O[CH:4](OCC)[CH2:5][NH:6][C:7]1[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:13][C:9]=2[N:10]=[CH:11][N:12]=1)C.Br.[CH:32]12[CH2:38][CH:35]([NH:36][CH2:37]1)[CH2:34][NH:33]2.C([BH3-])#N.[Na+]>C(O)(=O)C.ClCCCl>[CH:32]12[CH2:38][CH:35]([NH:36][CH2:37]1)[CH2:34][N:33]2[CH2:4][CH2:5][NH:6][C:7]1[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:13][C:9]=2[N:10]=[CH:11][N:12]=1

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 586032894-(2,2-Diethoxyethyl)amino-5,6-diphenyl furo[2,3-d]pyrimidineHCID 684608412,5-Diazabicyclo[2.2.1]heptane hydrobromide

Product 1

HCID 11711288[(2,5-Diaza-bicyclo[2.2.1]hept-2-yl)-ethyl]-(5,6-diphenyl-furo[2,3-d]pyrimidin-4-yl)-amine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

A mixture of 109 (10 mg, crude, 0.03 mmol for aldehyde) (made from compound 108 as in the preparation for 110) and 2,5-diaza-bicyclo[2.2.1]heptane hydrobromide (10 mg, 0.056 mmol) in 5% acetic acid solution in DCE (1 mL) was stirred at rt for 20 min. Sodium cyanoborohydride (20 mg, 0.32 mmol) was added and the reaction mixture was stirred at rt overnight. The reaction mixture was directly purified by HPLC, providing 136. MS: 412.2 (M+1).

Workup

  1. stirringthe reaction mixture was stirred at rt overnight
  2. customThe reaction mixture was directly purified by HPLC

Sources & evidence

ORD record
ord-095e869a275f44098eedb57054392d7f
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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