Diisopropylethylamine → HCID 117952500, compound

HRID 1499212Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:32][CH2:31][C:11]3([CH2:15][N:14]([C:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:17])[C@H:13]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4](Cl)[N:3]=1.[N:34]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[CH2:46][NH2:47])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C(N(C(C)C)CC)(C)C>CC(O)C>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:32][CH2:31][C:11]3([CH2:15][N:14]([C:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:17])[C@H:13]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([NH:47][CH2:46][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (S)-2-benzyl 3-ethyl 8-(2-amino-6-chloropyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (200 mg, 0.6 mmol) and [2-(1-piperidinyl)phenyl]methanamine (CAS#: 72752-54-6) (105 mg, 0.8 mmol) in i-PrOH (2 mL) was added diisopropylethyl amine (0.5 mL). The reaction was heated to 120° C. for 2 h followed by heating to 140° C. for 1 h under microwave conditions, then cooled to RT and concentrated in vacuo. Purification by normal phase silica gel column (EtOAc/heptane) provided (S)-2-benzyl 3-ethyl 8-(2-amino-6-((2-(piperidin-1-yl)benzyl)amino)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate as a white solid.

Workup

temperatureby heating to 140° C. for 1 h under microwave conditions
temperaturecooled to RT
concentrationconcentrated in vacuo
customPurification by normal phase silica gel column (EtOAc/heptane)

Sources & evidence

ORD record: ord-5d2400598c8a4903a3286d73ab2a87e9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199994B2

Reaction notes

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