N,N-Dimethylacrylamide → HCID 9916490, compound

HRID 2268375Notes

Reaction equation

HRID 2268375 reaction equation
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)=[C:5]([NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:4]=1.[CH3:37][N:38]([CH3:43])[C:39](=[O:42])[CH:40]=[CH2:41]>CO>[OH:17][C@@H:16]1[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13][C@H:12]1[N:9]1[CH:8]=[N:7][C:6]2[C:10]1=[N:11][C:3]([CH2:2][NH:1][CH2:41][CH2:40][C:39]([N:38]([CH3:43])[CH3:37])=[O:42])=[N:4][C:5]=2[NH:22][CH2:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 17587N,N-Dimethylacrylamide3×HCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Product 1

HCID 9916490HCID 9916490, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (200 mg, 0.39 mmol) was dissolved in stirred methanol (10 ml) and N,N-dimethylacrylamide (40 mg, 0.39 mmol) added. The reaction mixture was stirred for 120 hr at room temperature and then 50° C. for a further 24 hr. More N,N-dimethylacrylamide (9 mg, 0.1 mmol) was added and the reaction mixture was heated at 50° C. for 30 hr. A further portion of N,N-dimethylacrylamide (10 mg, 0.1 mmol) was added and the reaction mixture heated to 50° C. for a further 24 hr. The solvent was then removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (94:4:0.2) increasing in polarity to (93:7:0.3) to give the title compound (100 mg) as a foam. MS: 590 (MH+).

Workup

  1. wait50° C. for a further 24 hr
  2. temperaturethe reaction mixture was heated at 50° C. for 30 hr
  3. temperaturethe reaction mixture heated to 50° C. for a further 24 hr
  4. customThe solvent was then removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (94:4:0.2)
  6. temperatureincreasing in polarity to (93:7:0.3)

Sources & evidence

ORD record
ord-4694e035913a46f591d5b3e2ae49ef5d
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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