Sodium Bicarbonate → HCID 117952405, compound

HRID 1499275Notes

Reaction equation

[Br:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10](Cl)[N:9]=[C:8]([NH2:13])[N:7]=1.[CH2:19]1[C:23]2([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:22][C@@H:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:20]1[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35].C([O-])(O)=O.[Na+]>O1CCOCC1>[NH2:13][C:8]1[N:9]=[C:10]([N:26]2[CH2:25][CH2:24][C:23]3([CH2:19][N:20]([C:34]([O:36][CH2:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[O:35])[C@H:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:22]3)[CH2:28][CH2:27]2)[CH:11]=[C:6]([O:5][CH2:4][C:3]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:2]=2[Br:1])[N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-((2-bromo-4-chlorobenzyl)oxy)-6-chloropyrimidin-2-amine (300 mg, 1.1 mmol), (S)-2-benzyl 3-ethyl 2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (400 mg, 1.2 mmol), and NaHCO3 (550 mg, 7 mmol) in dioxane (5 mL) was heated to 100° C. for 12 h. The reaction was cooled to RT, concentrated in vacuo, and extracted with EtOAc. The combined organic layers were washed with brine, water, dried over Na2SO4, and concentrated in vacuo. Purification on normal phase silica gel (EtOAc/petroleum ether) provided (S)-2-benzyl 3-ethyl 8-(2-amino-6-((2-bromo-4-chlorobenzyl)oxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate as a white solid.

Workup

temperatureThe reaction was cooled to RT
concentrationconcentrated in vacuo
extractionextracted with EtOAc
washThe combined organic layers were washed with brine, water
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customPurification on normal phase silica gel (EtOAc/petroleum ether)

Sources & evidence

ORD record: ord-28535fcf79f04665a96850d0c8fcbc13
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199994B2

Reaction notes

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