Hydrochloric Acid → 2-chloro-9-methyl-6-((R)-3-methylmorpholin-4-yl)-9H-purine-8-carbaldehyde

HRID 1945692Notes

Reaction equation

HRID 1945692 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@H:13]2[CH3:18])[N:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CN([CH:32]=[O:33])C.Cl>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:32]=[O:33])[N:8]2[CH3:11])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@H:13]2[CH3:18])[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 2733832Lithium HexamethyldisilazideHCID 59605958HCID 59605958, compound

Product 1

HCID 596059322-chloro-9-methyl-6-((R)-3-methylmorpholin-4-yl)-9H-purine-8-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-9-methyl-6-((R)-3-methylmorpholin-4-yl)-9H-purine (550 mg, 2.05 mmol) in THF (20 mL) at −78° C. was added LiHMDS (3.1 mL, 3.08 mmol, 1M solution in THF). The resulting mixture was allowed to stir for 45 min before the addition of DMF (800 μL, 10.33 mmol). The reaction mixture was warmed to r.t. over 1.5 h then poured onto 0.5M HCl. The resulting precipitate was collected by filtration and washed with H2O then Et2O affording the title compound as a yellow solid (406 mg, 67%). LCMS (method H): RT 3.35 min [M+H]+ 296.3

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with H2O
  3. customRT 3.35 min [M+H]+ 296.3

Sources & evidence

ORD record
ord-1953801b50a449cf96cb50adc3bb85f2
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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