2,4-dichloro-5-(pyridin-2-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine → HCID 178454130, compound

HRID 577706Notes

Reaction equation

HRID 577706 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=2[N:7]=1.[C:26]([O:30][C:31](=[O:38])[NH:32][C@H:33]1[CH2:36][C@H:35]([OH:37])[CH2:34]1)([CH3:29])([CH3:28])[CH3:27]>O1CCCC1.CCOC(C)=O>[C:26]([O:30][C:31](=[O:38])[NH:32][C@H:33]1[CH2:36][C@H:35]([O:37][C:4]2[C:5]3[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=4)=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=3[N:7]=[C:2]([Cl:1])[N:3]=2)[CH2:34]1)([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 866796502,4-dichloro-5-(pyridin-2-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidineHCID 178454126HCID 178454126, compound

Product 1

HCID 178454130HCID 178454130, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-dichloro-5-(pyridin-2-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (318 mg, 0.804 mmol) in tetrahydrofuran (8 mL) was added tert-butyl(trans-3-hydroxycyclobutyl)carbamate and potassium hexamethyldisilizane (642 mg, 3.2 mmol) and the mixture stirred at ambient temperature for 1 hr. The reaction mixture was diluted with EtOAc (10 mL) and washed with water (20 mL). The aqueous layer was extracted with EtOAc (three×10 mL) and the combined organics were dried over MgSO4, filtered and stripped to give the title compound (485 mg, 110 yield). The crude material was used for the next step. m/z (APCI+) for C17H33N5O4ClSi 546.2 (M+H)+.

Workup

  1. washwashed with water (20 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (three×10 mL)
  3. dry with materialthe combined organics were dried over MgSO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-cb3e95d37ff84d2cb69d1788d3e60272
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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