(R)-3-Aminotetrahydrofuran → 2-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-{4-[(3R)-tetrahydro-3-furanylamino]butyl}-9H-purin-6-amine

HRID 2036363Notes

Reaction equation

HRID 2036363 reaction equation
[CH3:1][C@H:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([O:27][CH3:28])[N:13]2[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH:21]2[CH2:26]C[O:24][CH2:23][CH2:22]2)=[C:9]([NH2:29])[N:8]=1)[CH2:3][CH2:4][CH3:5].ClCCCCN1C(OC)=NC2C1=NC(O[C@@H](C)CCC)=NC=2N.O1CC[C@@H](N)C1>>[CH3:1][C@H:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([O:27][CH3:28])[N:13]2[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C@@H:21]2[CH2:22][CH2:23][O:24][CH2:26]2)=[C:9]([NH2:29])[N:8]=1)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 10996958(R)-3-AminotetrahydrofuranHCID 582909339-(4-Chlorobutyl)-2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amineHCID 582909342-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[4-(tetrahydro-2H-pyran-4-ylamino)butyl]-9H-purin-6-amine

Product 1

HCID 582909592-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-{4-[(3R)-tetrahydro-3-furanylamino]butyl}-9H-purin-6-amine

Conditions

Temperature
70 °C

Procedure

Prepared similarly to Intermediate 36 from 9-(4-chlorobutyl)-2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine and (3R)-tetrahydro-3-furanamine but with heating at 70° C. for an additional 20 hours.

Sources & evidence

ORD record
ord-a49b727e61cd492bb741f1d5910fdc77
Source dataset
uspto-grants-2013_11
Patent number
US08575181B2

Reaction notes

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