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Acetic Acid → 6-methyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydro-2H-pyran-4-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

HRID 1930660
Notes
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Reaction equation

HRID 1930660 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][CH:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]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:32](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[CH3:32][N:22]1[CH2:21][CH2:20][C:18]2[N:19]=[C:14]([NH:13][C:10]3[CH:11]=[CH:12][C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[CH3:1])=[CH:8][CH:9]=3)[N:15]=[C:16]([NH:24][CH2:25][CH:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[C:17]=2[CH2:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59333815N2-(4-(2-Methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydro-2H-pyran-4-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

Product 1

HCID 461997396-methyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydro-2H-pyran-4-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine
Yield 32.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N2-(4-(2-Methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydro-2H-pyran-4-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (49 mg, 0.12 mmol) was dissolved in methanol (3 mL). Acetic acid (6.69 μL, 0.12 mmol) was added followed by formaldehyde (8.70 μL, 0.12 mmol). The reaction mixture was stirred at room temperature for 15 minutes and sodium cyanoborohydride (7.34 mg, 0.12 mmol) was added. After 1 h the solvent was evaporated under reduced pressure, the crude purified twice by preparative HPLC (acidic system) yielding 6-methyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydro-2H-pyran-4-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (16.40 mg, 32.4%). MS (ES+) m/z 434.3 (M+H)+

Workup

  1. customAfter 1 h the solvent was evaporated under reduced pressure
  2. customthe crude purified twice by preparative HPLC (acidic system)

Sources & evidence

ORD record
ord-1a8800fc01994752bd994e8723604326
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188101B2

Reaction notes

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