Methanol → HCID 466050, compound

HRID 1720886Notes

Reaction equation

HRID 1720886 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH2:14])[C:5]2[N:11]=[C:10]([CH2:12]Br)[CH:9]=[CH:8][C:6]=2[N:7]=1.[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[K].CO>CC(N(C)C)=O.C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([NH2:14])[C:5]2[N:11]=[C:10]([CH2:12][S:21][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 7969ThiophenolHCID 5462222PotassiumHCID 133452266-(Bromomethyl)pyrido[3,2-d]pyrimidine-2,4-diamine

Product 1

HCID 466050HCID 466050, compoundYield 0.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 31374DimethylacetamideSolvent

Procedure

To a suspension of 7 (~2.5 mmol) in anhydrous dimethylacetamide was added 1 mL thiophenol (5 mmol) and 690 mg anhydrous potassium (5 mmol). After the suspension was stirred for 3 days, the spot of 7 disappeared from TLC. The Rf value of one of new spots which is assigned as 9 is 0.35 (in 2:8 methanol:chloroform). The solvent DMAC was removed under diminished pressure. The solid residue was washed with methanol three times and filtered. The combined liquid was added silica gel and then the methanol was evaporated to dryness. A small amount of product was separated through a dry column. 1HNMR, the product. After crystallization, 5 mg of pure product was obtained.

Workup

  1. customThe solvent DMAC was removed under diminished pressure
  2. washThe solid residue was washed with methanol three times
  3. filtrationfiltered
  4. additionThe combined liquid was added silica gel
  5. customthe methanol was evaporated to dryness
  6. customA small amount of product was separated through a dry column
  7. customAfter crystallization

Sources & evidence

ORD record
ord-5f1b32ee345c4a89a0768906f347f5ad
Source dataset
uspto-grants-1996_04
Patent number
US05508281

Reaction notes

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