Formaldehyde → HCID 58654382, compound

HRID 1170530Notes

Reaction equation

HRID 1170530 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][NH:8][CH:7]1[C:11]1[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[N:12]=1)=[O:5])[CH3:2].C=O.CO.[C:27](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O.C(O)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][N:8]([CH3:27])[CH:7]1[C:11]1[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[N:12]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 58654393HCID 58654393, compound

Product 1

HCID 58654382HCID 58654382, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2-(2-Imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidine-3-carboxylic acid ethyl ester (300 mg, 0.996 mmol), formaldehyde, 37 wt % in H2O (500 μL), methanol (8 mL) and acetic acid (550 μL) were all combined in a reaction vessel and stirred for 30 mins. Next, sodium triacetoxyborohydride (530 mg, 2.49 mmol) was added and the solution was allowed to stir at room temperature for an additional 30 mins. After this period of time, the reaction mixture was concentrated under vacuum, dissolved in ethyl acetate (75 mL) and poured into ice (25 mL). The pH was adjusted to pH=8 with 1M NaOH. The organic layer was partitioned from the aqueous layer, dried over Na2SO4 and concentrated down to afford the crude product. The product was purified by Flash Chromatography (0-10% methanol/DCM gradient) to afford 130 mg (42%) 2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-1-methyl-pyrrolidine-3-carboxylic acid ethyl ester. [M+H]+ 316.56.

Workup

  1. customall combined in a reaction vessel
  2. stirringto stir at room temperature for an additional 30 mins
  3. waitAfter this period of time
  4. concentrationthe reaction mixture was concentrated under vacuum
  5. dissolutiondissolved in ethyl acetate (75 mL)
  6. additionpoured into ice (25 mL)
  7. customThe organic layer was partitioned from the aqueous layer
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated down
  10. customto afford the crude product
  11. customThe product was purified by Flash Chromatography (0-10% methanol/DCM gradient)

Sources & evidence

ORD record
ord-84ad9f2858b74c73b875916056c14cff
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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