Cyano-borohydride → HCID 11294189, compound

HRID 1592068Notes

Reaction equation

HRID 1592068 reaction equation
[NH2:1][C:2]1[C:3]2[S:10][C:9]3[N:11]=[C:12]([N:18]4[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]4)[CH:13]=[C:14]([CH2:15][CH2:16][CH3:17])[C:8]=3[C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:25][CH2:26][C@H:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[OH:28].C([BH3-])#N>CN(C=O)C.C(O)(=O)C>[NH2:1][C:2]1[C:3]2[S:10][C:9]3[N:11]=[C:12]([N:18]4[CH2:19][CH2:20][CH:21]([NH:25][CH2:26][C@H:27]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[OH:28])[CH2:22][CH2:23]4)[CH:13]=[C:14]([CH2:15][CH2:16][CH3:17])[C:8]=3[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 498716Cyano-borohydrideHCID 643217(1S)-2-amino-1-phenylethan-1-olHCID 11416569HCID 11416569, compound

Product 1

HCID 11294189HCID 11294189, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

1-(4-Amino-9-propyl-pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-7-yl)-piperidin-4-one (Example 4) (341 mg, 1.00 mmol) and (S)-2-amino-1-phenylethanol (142 mg, 1.00 mmol) was dissolved in 10 mL of dry DMF. MP-Cyanoborohydride (0534 mg, 1.20 mmol) was added followed by 10 drops of glacial acetic acid. This mixture was shaken for 16 h. The resin was removed by filtration and washed with MeOH and dichloromethane. The filtrate was evaporated. The residue was treated with 2 M sodium carbonate solution. The resulting solid was collected by filtration and recrystalized from MeOH/acetonitrile to give the title compound as a pale-colored solid (0.260 g, 56%).

Workup

  1. customThe resin was removed by filtration
  2. washwashed with MeOH and dichloromethane
  3. customThe filtrate was evaporated
  4. additionThe residue was treated with 2 M sodium carbonate solution
  5. filtrationThe resulting solid was collected by filtration
  6. customrecrystalized from MeOH/acetonitrile

Sources & evidence

ORD record
ord-3c3697ba8aa845259f3d10b737ad67a3
Source dataset
uspto-grants-2007_11
Patent number
US07291733B2

Reaction notes

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