HCID 57474772, compound → HCID 57474769, compound

HRID 391691Notes

Reaction equation

HRID 391691 reaction equation
[CH2:1]([N:5]1[C:13](=[O:14])[NH:12][C:11]2[C:6]1=[N:7][C:8]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][Si](C(C)C)(C(C)C)C(C)C)[CH:20]=1)=[N:9][C:10]=2[C:15]([O:17]C)=O)[CH:2]([CH3:4])[CH3:3].[NH2:36]C1C(C(OC)=O)=NC(C2C=CC=C(O[Si](C(C)C)(C(C)C)C(C)C)C=2)=NC=1NC1C2C(=CC=CC=2)CC1>ClCCl>[OH:25][C:21]1[CH:20]=[C:19]([C:8]2[N:7]=[C:6]3[C:11]([NH:12][C:13](=[O:14])[N:5]3[CH2:1][CH:2]([CH3:3])[CH3:4])=[C:10]([C:15]([NH2:36])=[O:17])[N:9]=2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 57474772HCID 57474772, compoundHCID 68961932HCID 68961932, compound

Product 1

HCID 57474769HCID 57474769, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 9-isobutyl-8-oxo-2-(3-(triisopropylsilyloxy)phenyl)-8,9-dihydro-7H-purine-6-carboxylate. Methyl 5-amino-6-(2,3-dihydro-1H-inden-1-ylamino)-2-(3-(triisopropylsilyloxy)phenyl)pyrimidine-4-carboxylate (0.300 g, 0.635 mmol) and 1,1′-1,1′-carbonyldiimidazole (0.411 g, 2.54 mmol) in dichloromethane (25 mL) were reacted according to General Procedure F. The solution was condensed under reduced pressure and partitioned between water and ethyl acetate (3×). Organic fractions were combined and dried over magnesium sulfate, filtered and solvent removed under reduced pressure. The crude solid was diluted with methanol (15 mL) and sonicated. The resulting precipitate was filtered to afford the title compound (0.185 g, 85%). MS (ESI) m/z 268.2 [M+1]+.

Workup

  1. customcondensed under reduced pressure
  2. custompartitioned between water and ethyl acetate (3×)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customsolvent removed under reduced pressure
  6. additionThe crude solid was diluted with methanol (15 mL)
  7. customsonicated
  8. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-ea71826f4a384c7c84231e895891261e
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

Loading…