Formaldehyde → HCID 178499076, compound

HRID 2373526Notes

Reaction equation

HRID 2373526 reaction equation
C([O:9][C:10]1[C:11]([C:31]([O:33][CH3:34])=[O:32])=[N:12][C:13]([C:17]2([CH3:30])[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20][CH2:19][NH:18]2)=[N:14][C:15]=1[OH:16])(=O)C1C=CC=CC=1.[BH3-][C:36]#N.[Na+].C(O[Na])(C)=O.C=O>CO>[C:26]([O:25][C:23]([N:21]1[CH2:20][CH2:19][N:18]([CH3:36])[C:17]([C:13]2[N:12]=[C:11]([C:31]([O:33][CH3:34])=[O:32])[C:10]([OH:9])=[C:15]([OH:16])[N:14]=2)([CH3:30])[CH2:22]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178418247HCID 178418247, compoundHCID 178499078HCID 178499078, compound

Product 1

HCID 178499076HCID 178499076, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude material methyl 5-(benzoyloxy)-2-[4-(tert-butoxycarbonyl)-2-methylpiperazin-2-yl]-6-hydroxypyrimidine-4-carboxylate (C-44) obtained in step 1 was dissolved in MeOH, and NaCNBH3 (2.8 eq), AcONa (3.2 eq) and HCHO (37% in H2O, 4 eq) were added. The reaction mixture was stirred at room temperature. After 30′, the solvent was evaporated and the crude solid (C-45) obtained washed with Et2O.

Workup

  1. customAfter 30′, the solvent was evaporated
  2. customthe crude solid (C-45) obtained
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-0e88351d3f0149e8a42c97b7815b5ff4
Source dataset
uspto-grants-2008_12
Patent number
US07459452B2

Reaction notes

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