Valinol → HCID 9951550, compound

HRID 1831461Notes

Reaction equation

HRID 1831461 reaction equation
[C:1]1([CH2:7][S:8][C:9]2[N:10]=[C:11](Cl)[C:12]3[S:17][C:16]([NH2:18])=[N:15][C:13]=3[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:20][CH:21]([CH:24]([CH3:26])[CH3:25])[CH2:22][OH:23]>>[NH2:18][C:16]1[S:17][C:12]2[C:11]([NH:20][CH:21]([CH:24]([CH3:26])[CH3:25])[CH2:22][OH:23])=[N:10][C:9]([S:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:14][C:13]=2[N:15]=1

Participants

3

Reactant 2

HCID 79019ValinolHCID 112782745-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amine

Product 1

HCID 9951550HCID 9951550, compoundYield 24.1%

Conditions

Temperature
100 °C

Procedure

5-Phenylmethylthio-7-chloro-thiazolo[4,5-d]pyrimidin-2-ylamine (WO 00/09511) (100 mg, 0.32 mmol) and DL-2-amino-3-methyl-1-butanol (253 μL, 2.3 mmol) were suspended in anhydrous tetrahydrofaran (4 mL) and the reaction tube was capped. The solution was heated at 100° C. for 24 hours and was then allowed to cool down to room temperature. The solvent was evaporated in vacuo and the crude product was flash chromatographed on silica (eluent—ammonia:ethanol:dichloromethane, 1:8:91) followed by a second chromatography (gradient eluent—ammonia ethyl acetate: dichloromethane, 1:59:40 to 1:99:0) resulting in 29 mg (24% yield) of the title compound as a white solid.

Workup

  1. customthe reaction tube was capped
  2. temperatureto cool down to room temperature
  3. customThe solvent was evaporated in vacuo
  4. customchromatographed on silica (eluent—ammonia:ethanol:dichloromethane, 1:8:91)

Sources & evidence

ORD record
ord-d882f53ee8e346e9b93ae90739556a83
Source dataset
uspto-grants-2006_06
Patent number
US07067657B2

Reaction notes

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