Dimethylamine → HCID 86686630, compound

HRID 1850528Notes

Reaction equation

HRID 1850528 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([CH2:11][OH:12])[N:8]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:23])([CH3:22])[C:20]#[N:21])=[CH:15][CH:14]=3)[C:6]=2[N:7]=1.[CH3:24][NH:25][CH3:26].C1COCC1>CN(C=O)C.[Cl-].[Na+].O.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([C:11]([N:25]([CH3:26])[CH3:24])=[O:12])[N:8]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([C:20]#[N:21])([CH3:23])[CH3:22])=[CH:15][CH:14]=3)[C:6]=2[N:7]=1

Participants

7

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 86686629HCID 86686629, compound

Product 1

HCID 86686630HCID 86686630, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(4-(2-chloro-6-(hydroxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)phenyl)-2-methylpropanenitrile (589 mg, 1.8 mmol), manganese dioxide (7.8 gm, 90 mmol) and 2 M dimethylamine solution in THF (4.51 ml, 9 mmol) were combined in 6 mL dry DMF. Reaction was stirred for 3 hrs whereupon the reaction appeared complete by LC/MS. Reaction was poured into brine and extracted into EtOAc. Combined organics were washed with water followed by brine and then dried over sodium sulfate. Volatiles were removed and the residue purified by NPLC (10-100% ethyl acetate in heptane, Analogix) to yield the pure desired compound. (345 mg, 52%). MS 367.7 m/z

Workup

  1. customReaction
  2. customReaction
  3. extractionextracted into EtOAc
  4. washCombined organics were washed with water
  5. dry with materialdried over sodium sulfate
  6. customVolatiles were removed
  7. customthe residue purified by NPLC (10-100% ethyl acetate in heptane, Analogix)

Sources & evidence

ORD record
ord-c6bfa60ff09b4aed927b1a4857bab0ea
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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