2-Pentanamine → 6-Amino-2-[(1-methylbutyl)amino]-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-Purin-8-one

HRID 1011169Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([O:18]C)[N:8]2[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:4]([NH2:20])[N:3]=1.[NH2:21][CH:22]([CH2:24][CH2:25][CH3:26])[CH3:23]>C(O)CO.CCOC(C)=O.C(Cl)Cl>[NH2:20][C:4]1[N:3]=[C:2]([NH:21][CH:22]([CH3:23])[CH2:24][CH2:25][CH3:26])[N:10]=[C:9]2[C:5]=1[NH:6][C:7](=[O:18])[N:8]2[CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of 2-chloro-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (40 mg) in ethylene glycol (1.5 mL) was added 2-aminopentane (0.16 mL) and the mixture was heated in a microwave at 170° C. for 2×30 mins. A further portion of 2-aminopentane (0.08 mL) was added and the reaction was heated in a microwave at 180° C. for 30 mins. The mixture was taken up in EtOAc (15 mL) and was washed with water (3×15 mL). The organics were separated, dried over MgSO4, filtered and concentrated in vacuo to give a brown residue. This was taken up in DCM and concentrated in a vacuum oven to give the title compound as a brown solid (18 mg).

Workup

temperaturethe reaction was heated in a microwave at 180° C. for 30 mins
washwas washed with water (3×15 mL)
customThe organics were separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a brown residue
concentrationconcentrated in a vacuum oven

Sources & evidence

ORD record: ord-c156ed7c3e0a43878fa1c5cc4bae8eb0
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

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