4-Aminotetrahydropyran → 2-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[5-(tetrahydro-2H-pyran-4-ylamino)pentyl]-9H-purin-6-amine

HRID 2036360Notes

Reaction equation

C[C@H](OC1N=C2C(N=C(OC)N2CCCC[NH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=C(N)N=1)CCC.Cl[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:36]1[C:44]([O:45][CH3:46])=[N:43][C:42]2[C:37]1=[N:38][C:39]([O:48][C@@H:49]([CH3:53])[CH2:50][CH2:51][CH3:52])=[N:40][C:41]=2[NH2:47].O1CCC(N)CC1>>[CH3:53][C@H:49]([O:48][C:39]1[N:38]=[C:37]2[C:42]([N:43]=[C:44]([O:45][CH3:46])[N:36]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][NH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[C:41]([NH2:47])[N:40]=1)[CH2:50][CH2:51][CH3:52]

Participants

Reactant 3

HCID 4192234-Aminotetrahydropyran

HCID 582909342-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[4-(tetrahydro-2H-pyran-4-ylamino)butyl]-9H-purin-6-amine

HCID 59252634(S)-9-(5-chloropentyl)-8-methoxy-2-(pentan-2-yloxy)-9H-purin-6-amine

Product 1

HCID 672240132-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[5-(tetrahydro-2H-pyran-4-ylamino)pentyl]-9H-purin-6-amine

Conditions

Temperature: 70 °C

Procedure

Prepared similarly to Intermediate 36 from 9-(5-chloropentyl)-2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine and tetrahydro-2H-pyran-4-amine but with heating at 70° C. for an additional 20 hours.

Sources & evidence

ORD record: ord-efc4197f1d8a4708803af418c95357a4
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575181B2

Reaction notes

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