Chloroform → HCID 69180759, compound

HRID 133045Notes

Reaction equation

HRID 133045 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25][N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[CH:21][CH:20]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1.C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[N:26]1([CH2:25][C:22]2[CH:21]=[CH:20][C:19]([C:17]3[NH:16][C:12]4[N:13]=[CH:14][N:15]=[C:10]([NH:9][C:6]5[CH:5]=[CH:4][C:3](=[O:2])[NH:8][CH:7]=5)[C:11]=4[CH:18]=3)=[CH:24][CH:23]=2)[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 69179694HCID 69179694, compound

Product 1

HCID 69180759HCID 69180759, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To 84 mg (0.20 mmol) of (6-methoxy-pyridin-3-yl)-[6-(4-morpholin-4-ylmethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine and 10 ml chloroform in an ampoule under N2-atmosphere, 0.1 ml (0.73 mmol) Me3Sil is added. After stirring for 6 h at 70° C., diluted NaHCO3 solution and EtOAc is added to the suspension at RT. Stirring, filtration and washing with water yields the title compound; TLC (THF/methanol/conc. ammonia 90:10:1) Rf=0.23; MS-ES+: (M+H)+=403; HPLC (conditions see Examples 67-78) tR=4.7 min.

Workup

  1. stirringStirring
  2. filtrationfiltration
  3. washwashing with water

Sources & evidence

ORD record
ord-1d4a38b280b643aba3c56cb0d45c11d6
Source dataset
uspto-grants-2008_06
Patent number
US07390805B2

Reaction notes

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