Hydrochloric Acid → HCID 135667590, compound

HRID 1291273Notes

Reaction equation

HRID 1291273 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][N:13]3[C:17]4[N:18]=[C:19]([S:24][CH3:25])[N:20]=[C:21]([O:22]C)[C:16]=4[CH:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][N:13]3[C:17]4[N:18]=[C:19]([S:24][CH3:25])[NH:20][C:21](=[O:22])[C:16]=4[CH:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 18918839HCID 18918839, compound

Product 1

HCID 135667590HCID 135667590, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

Under argon gas, 7-[4-(4-chlorobenzoyl)benzyl]-4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine (0.615 g) was dissolved in dioxane (6 ml) followed by addition of 4,41-thiobis(6-t-butyl-m-cresol) (7 mg). Then, 0.5N-HCl (1.2 ml) was added and the mixture was stirred at 105° C. for 36 hours. Thereafter, 0.5N-HCl (1.2 ml) was added again and the mixture was further stirred at the same temperature as above for 24 hours. After cooling to room temperature, the precipitate was collected by filtration, washed with methanol and ether, and dried to provide the title compound (0.405 g) 1H-NMR (DMSO-d6) δ: 2.53(3H,s), 5.42(2H,s), 6.44(1H,d,J=3.4Hz), 7.15(1H,d,J=3.4Hz), 7.45(2H,d,J=8.OHz), 7.60(2H,d,J=8.4Hz), 7.72(2H,d,J=8.OHz), 7.73(2H,d,J=8.4Hz), 12.18(1H,s).

Workup

  1. stirringthe mixture was further stirred at the same temperature as above for 24 hours
  2. temperatureAfter cooling to room temperature
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with methanol and ether
  5. customdried

Sources & evidence

ORD record
ord-1a750235c29744eca417245bdce206d8
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…