Acetic Acid → HCID 46199582, compound

HRID 1930644Notes

Reaction equation

HRID 1930644 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 59333763HCID 59333763, compound

Product 1

HCID 46199582HCID 46199582, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5)-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 (55 mg, 0.14 mmol) was dissolved in methanol (3 mL). Acetic acid (7.76 μL, 0.14 mmol) was added followed by formaldehyde (10.10 μL, 0.14 mmol) and sodium cyanoborohydride (8.52 mg, 0.14 mmol). The reaction mixture was stirred for 1 h at room temperature and the solvent was evaporated under reduced pressure. The crude was purified by preparative HPLC yielding (S)-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 (19.30 mg, 33.9%). MS (ES+) m/z 417.8 (M−H)−

Workup

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

Sources & evidence

ORD record
ord-3aed23507aa14c248a2270f35909ed0d
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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