Tetrahydro-4H-pyran-4-ol → HCID 86726510, compound

HRID 1487683Notes

Reaction equation

HRID 1487683 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([NH:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)=[CH:9][N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:6]=2[N:7]=1.[O:30]1[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32][CH2:31]1.CC(C)([O-])C.[Na+]>O1CCOCC1.C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([O:36][CH:33]2[CH2:34][CH2:35][O:30][CH2:31][CH2:32]2)[C:5]2[C:10]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([NH:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)=[CH:9][N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:28])[CH3:27])[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 74956Tetrahydro-4H-pyran-4-olHCID 23676156Sodium t-butoxideHCID 86726509HCID 86726509, compound

Product 1

HCID 86726510HCID 86726510, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4-(2,4-dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-N-methylbenzamide (1 equiv), tetrahydro-2H-pyran-4-ol (1.1 equiv), and sodium tert-butoxide (1.2 equiv) in 1,4-dioxane (0.22 M) were combined in a sealable flask. The reaction mixture was put under a nitrogen atmosphere, the sealable flask was sealed, and the mixture was stirred at 70° C. for 16 h. The mixture was cooled to room temperature and concentrated to afford an oil, which was suspended in DCM and purified using flash chromatography (0-50% ethyl acetate in hexane) to afford the desired product (89% yield) as a clear oil. MS (ESI) m/z 517.5 [M+1]+.

Workup

  1. customthe sealable flask was sealed
  2. temperatureThe mixture was cooled to room temperature
  3. concentrationconcentrated
  4. customto afford an oil, which
  5. custompurified

Sources & evidence

ORD record
ord-120324a930914f298b53a746a3e4f717
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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