tert-Butylacrylamide → HCID 59975286, compound

HRID 2268389Notes

Reaction equation

HRID 2268389 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.[C:37]([NH:41][C:42](=[O:45])[CH:43]=[CH2:44])([CH3:40])([CH3:39])[CH3:38]>CO.ClCCl>[C:37]([NH:41][C:42](=[O:45])[CH2:43][CH2:44][NH: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:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:4]=1)([CH3:40])([CH3:39])[CH3:38]

Participants

5

Reactant 2

HCID 7877tert-ButylacrylamideHCID 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 59975286HCID 59975286, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

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) (250 mg, 0.48 mmol) was dissolved in stirred methanol (10 ml) and N-(tert-butyl)acrylamide (62 mg, 0.48 mmol) added. The reaction mixture was stirred for 24 hr at room temperature and then heated at reflux for 120 hr, at which time all solvent had evaporated. The residual reaction mixture was dissolved in dichloromethane and the solvent removed under reduced pressure, this procedure was repeated twice more and then the product purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (94:4:0.2) increasing in polarity to (93:7:0.3) to give the title compound (143 mg) as a foam. MS: 618 (MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 120 hr, at which time all solvent
  3. customhad evaporated
  4. customThe residual reaction mixture
  5. customthe solvent removed under reduced pressure
  6. customthe product purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (94:4:0.2)
  7. temperatureincreasing in polarity to (93:7:0.3)

Sources & evidence

ORD record
ord-14cbc97ef6ff47b8ae96ebf2e6991aac
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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