Ammonium Chloride → HCID 10390026, compound

HRID 720631Notes

Reaction equation

[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[NH:15][C:14]3[C:13](=[O:16])[N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11](=[O:24])[N:10]([CH2:25][CH2:26][CH2:27][CH3:28])[C:9]=3[N:8]=2)=[CH:4][CH:3]=1.CC1(C)OC(=O)[C:35]2([CH2:37][CH2:36]2)[C:34](=O)[O:33]1.[Cl-].[NH4+]>CN(C)C=O.O>[CH2:17]([N:12]1[C:13](=[O:16])[C:14]2[NH:15][C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([N:1]4[CH2:37][CH2:36][CH2:35][C:34]4=[O:33])=[CH:30][CH:29]=3)=[N:8][C:9]=2[N:10]([CH2:25][CH2:26][CH2:27][CH3:28])[C:11]1=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 8-(4-amino-benzyl)-1-benzyl-3-butyl-3,7-dihydro-purine-2,6-dione (60 mg) in N,N-dimethylformamide (2 mL) was added 6,6-dimethyl-5,7-dioxa-spiro[2.5]octane-4,8-dione (Lancaster) (34 mg) and the mixture heated to 100° C. under argon for 16 hrs. The reaction mixture was cooled to RT and poured into saturated aqueous ammonium chloride, diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Purification by chromatotron using a 2 mm silica plate eluted with 95:5 chloroform/methanol gave the desired product as a pale yellow solid (36 mg). MS, m/z(M+)=471.2272.

Workup

temperatureThe reaction mixture was cooled to RT
extractionextracted with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried (sodium sulfate)
concentrationconcentrated in vacuo
customPurification by chromatotron
washeluted with 95:5 chloroform/methanol

Sources & evidence

ORD record: ord-63d3eaae6e434dc29bfd1db04763da84
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135475B2

Reaction notes

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