Hydrogen Bromide → HCID 87285205, compound

HRID 2252693Notes

Reaction equation

HRID 2252693 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][O:10][C@@H:11]1[C@@:17]([CH3:29])([CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[O:16][C@H:13](OC)[C@:12]1([CH3:31])[OH:30].Br.[Cl:33][C:34]1[N:39]=[CH:38][NH:37][C:36]2=[N:40][CH:41]=[CH:42][C:35]=12.[OH-].[K+]>CN1CCCC1=O.C1(C)C=CC=CC=1>[Cl:33][C:34]1[C:35]2[CH:42]=[CH:41][N:40]([C@@H:13]3[O:16][C@:17]([CH3:29])([CH2:18][O:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])[C@@H:11]([O:10][CH2:9][C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])[C@@:12]3([CH3:31])[OH:30])[C:36]=2[N:37]=[CH:38][N:39]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 14797Potassium HydroxideHCID 67142734HCID 67142734, compoundHCID 178418725HCID 178418725, compound

Product 1

HCID 87285205HCID 87285205, compoundYield 32.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the compound from Step C (0.70 g, 1.3 mmol) was added HBr (5.7 M in acetic acid, 2 mL). The resulting solution was stirred at room temperature for 1 h, evaporated in vacuo and co-evaporated with anhydrous toluene (3×10 mL). 4-Chloro-1H-pyrrolo[2,3-d]pyrimidine (0.5 g, 3.3 mmol) and powdered KOH (85%, 150 mg, 2.3 mmol) were stirred in 1-methyl-2-pyrrolidinone (5 mL) for 30 min and the mixture was co-evaporated with toluene (10 mL). The resulting solution was poured into the above bromo sugar residue and the mixture was stirred overnight. The mixture was diluted with toluene (50 mL), washed with water (3×50 mL) and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with EtOAc/Hexane (15/85) to afford a solid (270 mg).

Workup

  1. customevaporated in vacuo and co-evaporated with anhydrous toluene (3×10 mL)
  2. stirringthe mixture was stirred overnight
  3. washwashed with water (3×50 mL)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica gel eluting with EtOAc/Hexane (15/85)

Sources & evidence

ORD record
ord-34528b3af16b47d8a4fa83292111aa8c
Source dataset
uspto-grants-2008_01
Patent number
US07323453B2

Reaction notes

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