2-(Dimethylamino)ethanol → HCID 59540969, compound

HRID 1677544Notes

Reaction equation

HRID 1677544 reaction equation
[CH3:1][C:2]1([CH3:40])[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([C:17]3[N:18]=[C:19]4[C:25]([C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:24][N:23]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:20]4=[N:21][CH:22]=3)[CH:10]=[C:11]([O:13][CH2:14]OC)[CH:12]=2)[CH2:3]1.[CH3:41][N:42]([CH3:46])[CH2:43]CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:41][N:42]([CH3:46])[CH2:43][CH2:14][O:13][C:11]1[CH:10]=[C:9]([C:17]2[N:18]=[C:19]3[C:25]([C:26](=[O:31])[C:27]([CH3:28])([CH3:29])[CH3:30])=[CH:24][N:23]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:38])([CH3:37])[CH3:39])[C:20]3=[N:21][CH:22]=2)[CH:8]=[C:7]([N:4]2[CH2:5][CH2:6][C:2]([CH3:40])([CH3:1])[CH2:3]2)[CH:12]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanol3×HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 59540909HCID 59540909, compound

Product 1

HCID 59540969HCID 59540969, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask was charged with 1-[2-[3-(3,3-dimethyl-pyrrolidin-1-yl)-5-methoxymethoxy-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (90 mg, 0.17 mmol), 2-dimethylamino-ethanol (reagent A, 0.04 ml, 0.34 mmol) and triphenylphosphine (reagent B, 90 mg, 0.34 mmol). THF (2 ml) was added under nitrogen atmosphere. Diisopropyl azodicarboxylate (reagent C, 0.07 ml, 0.34 mmol) was added via syringe and the material was stirred. After 1 hour a further 2 equivalents each of reagents A, B and C were added. The mixture was stirred overnight. The crude was loaded onto 2 preparative TLC plates eluting with 3% MeOH in dichloromethane. The plates were dried and re-developed with the solvent system. This process was repeated once more and then product band was collected providing 1-[2-[3-(2-dimethylamino-ethoxy)-5-(3,3-dimethyl-pyrrolidin-1-yl)-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one, 56 mg, as a golden yellow viscous oil.

Workup

  1. stirringThe mixture was stirred overnight
  2. washeluting with 3% MeOH in dichloromethane
  3. customThe plates were dried and re-developed with the solvent system
  4. customproduct band was collected

Sources & evidence

ORD record
ord-f72be0105a0a465a858280b716071f22
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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