2-Methylpyridine → HCID 18799588, compound

HRID 1637783Notes

Reaction equation

HRID 1637783 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][CH2:9]O[Si](C)(C)C(C)(C)C)=[C:6](O)[N:5]=[C:4]([S:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[N:3]=1.N1C=CC=CC=1C.P(Cl)(Cl)([Cl:40])=O>>[Cl:40][C:6]1[C:7]2[CH2:8][CH2:9][NH:1][C:2]=2[N:3]=[C:4]([S:19][CH2:20][C:21]2[C:22]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:28]=[CH:29][CH:30]=2)[N:5]=1

Participants

4

Reactant 3

HCID 79752-MethylpyridineHCID 24813Phosphorus oxychlorideHCID 178455197HCID 178455197, compound

Product 1

HCID 18799588HCID 18799588, compound

Conditions

Temperature
22 °C

Procedure

2-(4-amino-6-hydroxy-2-(2-naphthylmethyl)thio-5-pyrimidinyl)-1-(dimethyl-tert-butylsilyloxy)ethane (Cpd #280; 104 mg, 0.23 mmol) is treated with 2-picoline (28 μL, 0.28 mmol) and phosphorus oxychloride (0.22 ml, 2.3 mmol). The solution is heated to reflux for 2 hours, stirred overnight at 22° C. then heated again to reflux for an additional hour. The solution was cooled and ice is added. The resultant solid was filtered, washed with cold 50% ethanol, and dried under vacuum. The recovered solids, 81 mg are purified by chromatography (SiO2, 4:1 hexane/ethyl acetate): 64 mg (0.19 mmol, 85%), mp 107-110° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 2 hours
  3. temperaturethen heated again
  4. temperatureto reflux for an additional hour
  5. temperatureThe solution was cooled
  6. additionice is added
  7. filtrationThe resultant solid was filtered
  8. washwashed with cold 50% ethanol
  9. customdried under vacuum
  10. customThe recovered solids, 81 mg are purified by chromatography (SiO2, 4:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b256285191a94aa19654502c862c0767
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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