2-Cyclopropylethan-1-ol → 2-[(2-Cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1010976Notes

Reaction equation

[CH:1]1([CH2:4][CH2:5][OH:6])[CH2:3][CH2:2]1.CC(C)([O-])C.[Na+].Cl[C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:16]([NH2:29])[N:15]=1>COCCOC>[CH:1]1([CH2:4][CH2:5][O:6][C:14]2[N:22]=[C:21]3[C:17]([N:18]=[CH:19][N:20]3[CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)=[C:16]([NH2:29])[N:15]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of 2-cyclopropylethanol (3.45 g) in DME (20 mL) was added sodium tert-butoxide (3.86 g) gradually. The reaction was stirred under nitrogen for 30 mins, then 2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (2.54 g) and DME (20 mL) were added. The reaction was heated to reflux (110° C.) overnight, then for another 8 h. The reaction was quenched into water (100 mL) and extracted with EtOAc (2×100 mL). The organics were combined and washed with brine (100 mL) and dried using a hydrophobic frit. The resultant oil was azeotroped with toluene (×2) to give a gum. This was triturated with Et2O (cooled CO2/acetone bath) until the title compound was obtained as a yellow powder (1.579 g) which was placed under high vacuum for 24 h.

Workup

temperatureThe reaction was heated
waitfor another 8 h
customThe reaction was quenched into water (100 mL)
extractionextracted with EtOAc (2×100 mL)
washwashed with brine (100 mL)
customdried
customThe resultant oil was azeotroped with toluene (×2)
customto give a gum
customThis was triturated with Et2O (cooled CO2/acetone bath) until the title compound

Sources & evidence

ORD record: ord-d06c4f06014144f39cabff78552b5e79
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977344B2

Reaction notes

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