Hexane isopropanol diethylamine → HCID 59834841, compound

HRID 271373Notes

Reaction equation

HRID 271373 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C@H:12]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18]3[N:23]=[CH:22][N:21]=[C:20]4[NH:24][N:25]=[CH:26][C:19]=34)[CH2:13]2)=[CH:5][CH:4]=1.CCCCCC.CC(O)C.C(NCC)C>>[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C@H:12]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18]3[N:23]=[CH:22][N:21]=[C:20]4[NH:24][N:25]=[CH:26][C:19]=34)[CH2:13]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 21973129Hexane isopropanol diethylamineHCID 69274803HCID 69274803, compound

Product 1

HCID 59834841HCID 59834841, compound

Procedure

Racemic N-[trans-3-[2-(4-methylphenyl)ethoxy]cyclopentyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrochloride was resolved by preparative chiral HPLC (Chiralcel OJ column, 5×50 mm, hexane: 2-propanol: diethylamine (40:60:0.1), 70 ml/min. The first enantiomer to elute was (+)-N-[trans-3-[2-(4-methylphenyl)ethoxy]cyclopentyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine (74 mg) as a white solid. Mass spec.: 338.3 (M+1). [α]D=+16° (c=0.214, methanol).

Workup

  1. washThe first enantiomer to elute

Sources & evidence

ORD record
ord-33911e1f3c0e4553a6ff8cd6e06013fb
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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