Formic Acid → HCID 86683381, compound

HRID 2173655Notes

Reaction equation

HRID 2173655 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[C:8]([C:12]1[N:13]=[C:14](Cl)[C:15]2[N:20]=[N:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C:16]=2[N:17]=1)([CH3:11])([CH3:10])[CH3:9].C(O)=O>CN(C=O)C>[C:8]([C:12]1[N:13]=[C:14]([O:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)[C:15]2[N:20]=[N:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C:16]=2[N:17]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 866832845-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Product 1

HCID 86683381HCID 86683381, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of cyclobutanol (173 mg, 2.4 mmol) and NaH (4.8 mg, 0.12 mmol) in DMF (1 mL) was stirred for 30 min at room temperature. 5-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (26.9 mg, 0.08 mmol) was added and the mixture was stirred at room temperature overnight. Formic acid added and the mixture was subjected to preparative HPLC purification on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The product containing fractions were evaporated to yield 4 mg (13%) of the title compound. MS(m/e): 372.3.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customthe mixture was subjected to preparative HPLC purification on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and formic acid
  5. additionThe product containing fractions
  6. customwere evaporated

Sources & evidence

ORD record
ord-7adcf5fdb0774b01b33c19d2a4a9a8c4
Source dataset
uspto-grants-2015_06
Patent number
US09056866B2

Reaction notes

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