Allyl Alcohol → HCID 59286706, compound

HRID 1091552Notes

Reaction equation

HRID 1091552 reaction equation
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([C:23](=[O:26])[NH:24][CH3:25])=[CH:19][C:18]=4[O:27][CH3:28])[N:12]=[CH:11][C:10]=3[N:9]3[CH:29]=[N:30][C:31]([C:32]([OH:34])=[O:33])=[C:8]3[C@H:7]2[CH2:35][CH3:36])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:49](O)[CH:50]=[CH2:51]>CN(C=O)C>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([C:23](=[O:26])[NH:24][CH3:25])=[CH:19][C:18]=4[O:27][CH3:28])[N:12]=[CH:11][C:10]=3[N:9]3[CH:29]=[N:30][C:31]([C:32]([O:34][CH2:51][CH:50]=[CH2:49])=[O:33])=[C:8]3[C@H:7]2[CH2:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 682631,1'-CarbonyldiimidazoleHCID 24958894HCID 24958894, compound

Product 1

HCID 59286706HCID 59286706, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
42.5 °C

Procedure

(R)-5-cyclopentyl-6-ethyl-3-(2-methoxy-4-(methylcarbamoyl)phenylamino)-5,6-dihydroimidazo[1,5-f]pteridine-7-carboxylic acid 1-2 (44 mg, 0.09 mmol) in DMF (0.5 mL) was treated with carbonyldiimidazole (19 mg, 0.12 mmol) and stirred at 40-45° C. for 40 minutes. Allyl alcohol (1 ml, 14.7 mmol) was then added and the reaction mixture was stirred at 40° C. for 18 hours. The mixture was partitioned between an aqueous solution of sodium carbonate and ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and concentrated to give the desired compound as a pale brown solid (37 mg, 77% yield); LC/MS M+1 (obs.) 532.68, LC/MS M-1 (obs.) 530.81.

Workup

  1. stirringthe reaction mixture was stirred at 40° C. for 18 hours
  2. customThe mixture was partitioned between an aqueous solution of sodium carbonate and ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bf17e9e84e684b0fb37c181159656608
Source dataset
uspto-grants-2012_03
Patent number
US08129387B2

Reaction notes

Loading…