Tetrahydrofuran → (S)-1-ethyl-3-(4-(7-(4-hydroxybutyl)-4-(3-methylmorpholino)-6,7,8,9-tetrahydro-5H-pyrimido[5,4-d]azepin-2-yl)phenyl)urea

HRID 1697969Notes

Reaction equation

HRID 1697969 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH:25]3[CH3:30])[C:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21][C:22]=3[N:23]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].[CH2:31]1[CH2:35][O:34][CH2:33][CH2:32]1>>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[C:16]3[CH2:17][CH2:18][N:19]([CH2:35][CH2:31][CH2:32][CH2:33][OH:34])[CH2:20][CH2:21][C:22]=3[N:23]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 671766001-ethyl-3-(4-(4-(3-methylmorpholino)-6,7,8,9-tetrahydro-5H-pyrimido[5,4-d]azepin-2-yl)phenyl)urea

Product 1

HCID 59239598(S)-1-ethyl-3-(4-(7-(4-hydroxybutyl)-4-(3-methylmorpholino)-6,7,8,9-tetrahydro-5H-pyrimido[5,4-d]azepin-2-yl)phenyl)urea

Procedure

During the synthesis of S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-6,7,8,9-tetrahydro-5H-pyrimido[5,4-d]azepin-2-yl)phenyl)urea (Step 3 of Example 286), the title compound sl (a white powder) was obtained as a by-product due to the oxidation of THF during long-term storage: 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=8.6 Hz, 2H), 7.36 (d, J=8.7 Hz, 2H), 6.33 (s, 1H), 4.62 (m, 1H), 3.89-3.55 (m, 6H), 3.39-3.15 (m, 5H), 2.98-2.52 (m, 7H), 1.74 (m, 8H), 1.33-1.02 (m, 6H); LC-MS m/z=483 (M+H).

Sources & evidence

ORD record
ord-00d00885704f445aad07ccd85661f45e
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

Loading…