Acetic Acid → HCID 178432898, compound

HRID 1930551Notes

Reaction equation

HRID 1930551 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]([OH:24])[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=O.[C:27](O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[CH3:27][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]([OH:24])[C:17]=2[CH2:23]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178432897HCID 178432897, compound

Product 1

HCID 178432898HCID 178432898, compoundYield 345.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ol (1.4 g, 4.34 mmol, Example 9c), formaldehyde (0.423 g, 5.21 mmol) and acetic acid (0.025 mL, 0.43 mmol) in MeOH (25 mL) was stirred for 10 min. Sodium cyanoborohydride (0.273 g, 4.34 mmol) was added and the reaction was stirred for an additional 10 min after which water (2 mL) was added. Solvent was evaporated and EtOAc (2 mL) was added followed by the addition of potassium carbonate solution (sat. aq., 1 mL). The solution was stirred and the formed precipitate was filtered off to give 6-methyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ol (0.500 g, 34.2%).

Workup

  1. additionwas added
  2. customSolvent was evaporated
  3. additionEtOAc (2 mL) was added
  4. additionfollowed by the addition of potassium carbonate solution (sat. aq., 1 mL)
  5. stirringThe solution was stirred
  6. filtrationthe formed precipitate was filtered off

Sources & evidence

ORD record
ord-54e519d8164d494ebe4272eae4040891
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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