Cesium carbonate → HCID 85827663, compound

HRID 1295469Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:4]=1[CH2:5][C:6]1[NH:7][C:8]2[C:13]([N:14]=1)=[C:12]([NH2:15])[N:11]=[C:10]([NH2:16])[N:9]=2.N1C=C2C(N=CN2)=NC=1.Cl[CH2:33][CH2:34][CH2:35][C:36]#[CH:37].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:4]=1[CH2:5][C:6]1[N:7]([CH2:37][CH2:36][CH2:35][C:34]#[CH:33])[C:8]2[C:13]([N:14]=1)=[C:12]([NH2:15])[N:11]=[C:10]([NH2:16])[N:9]=2

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of the purine 8-(2,5-Dimethoxy-benzyl)-9H-purine-2,6-diamine (19.0 g, 63 mmol), 5-chloro-pent-1-yne (12.3 ml, 116 mmol), and Cs2CO3 (37.8 g, 116 mmol) in DMF (180 g) was heated to 50° C. for 16 h. Filtration and washing (2×200 ml H2O) afforded some desired product (5.8 g, 25%). The mother liquor was concentrated, diluted with EtOAc, and heated to reflux for 1 h to yield additional product (6.0 g, 26%). After cooling to room temperature, addition of 1 volume hexane to the EtOAc mother liquor gave additional product (2.6 g, 11%). Final work-up (CH2Cl2:MeOH 4:1—water) yielded additional product (5.3 g, containing 1 equivalent penty-4-yn-1-ol, 18%). Rf=0.65 in 1:10 MeOH:EtOAc. 1H NMR (DMSO-d6) δ 6.92 (d, J=8.9 Hz, 1H), 6.98 (dd, J=8.9 & 3.0 Hz, 1H), 6.59 (s, J=2.9 Hz, 1H), 6.58-6.53 (br. s, 2H), 5.72-5.68 (br. s, 2H), 4.02 (s, 2H), 3.92 (t, J=7.4 Hz, 2H), 3.73 (s, 3H), 3.62 (s, 3H), 2.84 (t, J=2.5 Hz, 1H), 2.13 (td, J=7.0 & 1.7 Hz, 2H), 1.74 (quint., J=7.3 Hz, 2H); MS 367 (M+1).

Workup

filtrationFiltration
washwashing (2×200 ml H2O)

Sources & evidence

ORD record: ord-24e06bf509204959ae27cf9a2af9f16d
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241890B2

Reaction notes

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