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

HRID 1930634
Notes
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Reaction equation

HRID 1930634 reaction equation
[CH:1]1([NH:7][C:8]2[C:9]3[CH2:30][NH:29][CH2:28][CH2:27][C:10]=3[N:11]=[C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[CH:24][N:23]=[C:22]4[CH3:26])=[CH:17][CH:16]=3)[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:31](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[CH:1]1([NH:7][C:8]2[C:9]3[CH2:30][N:29]([CH3:31])[CH2:28][CH2:27][C:10]=3[N:11]=[C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[CH:24][N:23]=[C:22]4[CH3:26])=[CH:17][CH:16]=3)[N:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59333805N4-Cyclohexyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

Product 1

HCID 46199431N4-cyclohexyl-6-methyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine
Yield 15.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N4-Cyclohexyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (93 mg, 0.23 mmol) was dissolved in methanol (3 mL). Acetic acid (0.013 mL, 0.23 mmol) was added followed by formaldehyde (0.017 mL, 0.23 mmol) and sodium cyanoborohydride (14.48 mg, 0.23 mmol). The reaction mixture was stirred at room temperature for 1 h and the solvent was evaporated under reduced pressure. The crude material was dissolved in few drops of methanol, filtered and purified by preparative HPLC (acidic system) yielding N4-cyclohexyl-6-methyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (15.00 mg, 15.59%). MS (ES+) m/z 418.2 (M+H)+

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe crude material was dissolved in few drops of methanol
  3. filtrationfiltered
  4. custompurified by preparative HPLC (acidic system)

Sources & evidence

ORD record
ord-09d5c942db3846b18160e583f1aebf87
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188101B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes