Dichloromethane → 4-Chloro-2,5,6,7-tetramethyl-5H-pyrrolo[3,2-d]pyrimidine

HRID 1772179Notes

Reaction equation

HRID 1772179 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=O)[C:5]2[N:10]([CH3:11])[C:9]([CH3:12])=[C:8]([CH3:13])[C:6]=2[N:7]=1.O=P(Cl)(Cl)[Cl:17].C(Cl)Cl.[OH-].[Na+]>O>[Cl:17][C:4]1[C:5]2[N:10]([CH3:11])[C:9]([CH3:12])=[C:8]([CH3:13])[C:6]=2[N:7]=[C:2]([CH3:1])[N:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 1360300782,5,6,7-Tetramethyl-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one

Product 1

HCID 599394834-Chloro-2,5,6,7-tetramethyl-5H-pyrrolo[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,5,6,7-tetramethyl-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one N9b (0.334 g, 1.75 mmol) and POCl3 (4 ml) is stirred at 100° C. for 17 hours. At 0° C. DCM (30 ml) and aqueous sodium hydroxide (1 mol/1, 20 ml) is added under vigorous stirring. The water phase is made basic with an aqueous solution of sodium hydroxide (1 mol/l) and extracted with DCM. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is used without further purification. Yield: 330 mg (90%). HPLC-MS: M+H=210; tR=0.92 min (METHOD—1).

Workup

  1. customAt 0° C
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe product is used without further purification

Sources & evidence

ORD record
ord-82c151c0ab304f97af09c059e91f951d
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

Loading…