3-amino-2-ethyl-3H,4H-thieno[2,3-d]pyrimidin-4-one → HCID 49872535, compound

HRID 1853404Notes

Reaction equation

HRID 1853404 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][S:11][C:5]=2[N:4]=[C:3]1[CH2:12][CH3:13].[C:14]12([CH2:24][C:25](Cl)=[O:26])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2>>[C:14]12([CH2:24][C:25]([NH:1][N:2]3[C:7](=[O:8])[C:6]4[CH:9]=[CH:10][S:11][C:5]=4[N:4]=[C:3]3[CH2:12][CH3:13])=[O:26])[CH2:21][CH:20]3[CH2:19][CH:18]([CH2:17][CH:16]([CH2:22]3)[CH2:15]1)[CH2:23]2

Participants

3

Reactant 2

HCID 21329803-amino-2-ethyl-3H,4H-thieno[2,3-d]pyrimidin-4-oneHCID 27718821-Adamantaneacetyl chloride

Product 1

HCID 49872535HCID 49872535, compound

Procedure

3-Amino-2-ethylthieno[2,3-d]pyrimidin-4(3H)-one and 1-adamantaneacetyl chloride were reacted as described in Example 5 to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.20 (t, J=7.3 Hz, 3H), 1.59-1.74 (m, 12H), 1.93-1.98 (m, 3H), 2.08-2.18 (m, 2H), 2.56-2.80 (m, 2H), 7.39 (d, J=6.0 Hz, 1H), 7.59 (d, J=6.0 Hz, 1H), 10.83 (s, 1H) ppm; MS (DCI/NH3) m/z 372 (M+H)+; Elemental Analysis: Calculated for C20H25N3O2S: C, 63.74; H, 6.85; N, 11.15. Found: C, 63.77; H, 6.89; N, 11.13.

Sources & evidence

ORD record
ord-e3db7420138240a3b22f098208217a74
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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