Formaldehyde → HCID 135544114, compound

HRID 354192Notes

Reaction equation

HRID 354192 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:15]2[NH:16][C:17](=[O:32])[C:18]3[C:19](=[C:21]([CH2:30][CH3:31])[N:22]([CH:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)[N:23]=3)[N:20]=2)[C:7]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:8][CH:9]=1)(=[O:3])[CH3:2].C=O.[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:1]([C:4]1[CH:5]=[C:6]([C:15]2[NH:16][C:17](=[O:32])[C:18]3[C:19](=[C:21]([CH2:30][CH3:31])[N:22]([CH:24]4[CH2:29][CH2:28][N:27]([CH3:35])[CH2:26][CH2:25]4)[N:23]=3)[N:20]=2)[C:7]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 712Formaldehyde3×HCID 5049666Sodium triacetoxyborohydride3×HCID 135520500HCID 135520500, compound

Product 1

HCID 135544114HCID 135544114, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(5-Acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-(4-piperidinyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Example 49) (100 mg, 0.23 mmol) was dissolved in dichloromethane (10 mL) and formaldehyde (27 mg, 0.01 mL of a 37-41% solution) was added. After 30 min stirring sodium triacetoxyborohydride (108 mg, 0.51 mmol) was added and stirring continued for 14 h. Further formaldehyde (0.01 mL of 37-41% solution) and sodium triacetoxyborohydride (108 mg, 0.51 mmol) were added and stirring continued for a further 4.5 h. Starting material still remained so further formaldehyde (0.01 mL of 37-41% solution) and sodium triacetoxyborohydride (108 mg, 0.51 mmol) were added and stirring continued for a further 18 h. The reaction mixture was diluted with dichloromethane, washed with sodium bicarbonate solution then brine, dried (MgSO4) and concentrated. Purification by flash column chromatography (elution with 94:6:0.6 dichloromethane/methanol/0.88 ammonia) gave the product (41 mg) as a white solid.

Workup

  1. additionwas added
  2. stirringstirring
  3. waitcontinued for a further 4.5 h
  4. additionwere added
  5. stirringstirring
  6. waitcontinued for a further 18 h
  7. washwashed with sodium bicarbonate solution
  8. dry with materialbrine, dried (MgSO4)
  9. concentrationconcentrated
  10. customPurification
  11. washby flash column chromatography (elution with 94:6:0.6 dichloromethane/methanol/0.88 ammonia)

Sources & evidence

ORD record
ord-c8594747ba014c9880187b73ed10a93a
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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