Acetic Acid → HCID 46199583, compound

HRID 1930647Notes

Reaction equation

HRID 1930647 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16]([NH:24][CH2:25][C@H:26]4[CH2:30][CH2:29][CH2:28][O:27]4)[C:17]4[CH2:23][NH:22][CH2:21][CH2:20][C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[C:31](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[CH3:31][N:22]1[CH2:21][CH2:20][C:18]2[N:19]=[C:14]([NH:13][C:10]3[CH:9]=[CH:8][C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[CH3:1])=[CH:12][CH:11]=3)[N:15]=[C:16]([NH:24][CH2:25][C@H:26]3[CH2:30][CH2:29][CH2:28][O:27]3)[C:17]=2[CH2:23]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59333714HCID 59333714, compound

Product 1

HCID 46199583HCID 46199583, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-N2-(4-(2-Methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (56 mg, 0.14 mmol) was dissolved in methanol (3 mL). Acetic acid (7.91 μL, 0.14 mmol) was added followed by formaldehyde (10.28 μL, 0.14 mmol) and sodium cyanoborohydride (8.68 mg, 0.14 mmol). The reaction mixture was stirred at room temperature for 1 h and the solvent was evaporated under reduced pressure. The crude was purified by preparative HPLC yielding (R)-6-methyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (18.70 mg, 32.3%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-689f29be581d4141bd3ecd657fdb69e9
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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