HCID 58034294, compound → HCID 58034578, compound

HRID 1914854Notes

Reaction equation

HRID 1914854 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=[C:6]2[N:5]=[CH:4][C:3]=1[CH2:15][OH:16]>C1COCC1.C(Cl)(Cl)Cl.O=[Mn]=O>[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([CH3:12])([CH3:14])[CH3:13])[CH:10]=[C:6]2[N:5]=[CH:4][C:3]=1[CH:15]=[O:16]

Participants

5

Reactant 1

HCID 58034294HCID 58034294, compound

Product 1

HCID 58034578HCID 58034578, compound

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (7-amino-2-tert-butylpyrazolo[1,5-a]pyrimidin-6-yl)methanol (380 mg, 1.73 mmol, 1 eq.) and MnO2 (1.5 g, 17.25 mmol, 10 eq.) in THF (6 mL) and CHCl3 (12 ml) was stirred for about 36 h at 25° C. under nitrogen. MnO2 was filtered and washed with 15% MeOH in CHCl3 (˜100 mL) and 30% MeOH in CHCl3 (˜100 mL) until no additional product was observed through analysis of the filtrates by TLC. The filtrates were combined and concentrated under vacuum to give Compound [CCXXXVII] as a yellow solid: LCMS (m/e) 219 (M+H); 1H NMR (300 MHz, DMSO, δ, ppm) 9.87 (s, 1H), 8.99-8.82 (s, 2H), 8.50 (s, 1H), 6.52 (s, 1H), 1.38 (s, 9H).

Workup

  1. filtrationMnO2 was filtered
  2. washwashed with 15% MeOH in CHCl3 (˜100 mL) and 30% MeOH in CHCl3 (˜100 mL) until no additional product
  3. concentrationconcentrated under vacuum
  4. customto give Compound [CCXXXVII] as a yellow solid

Sources & evidence

ORD record
ord-7e68652de98c4a1ba68ad0b16a619c0f
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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