Dimethylformamide → HCID 59239537, compound

HRID 1697996Notes

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:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:16]3[CH2:22][CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].[CH3:29]N(C)C=O.C(N(CC)C(C)C)(C)C.[CH3:43][C:44]([CH3:49])([CH3:48])[C:45](Cl)=[O:46]>>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[C:16]3[CH2:22][CH2:21][N:20]([C:45](=[O:46])[C:44]([CH3:49])([CH3:48])[CH3:43])[CH2:19][C:17]=3[N:18]=2)=[CH:11][C:12]=1[CH3:29])=[O:5])[CH3:2]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 62493Pivaloyl chloride

HCID 81531Diisopropylethylamine

HCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 59239537HCID 59239537, compound

Procedure

1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.042 g, 0.11 mmol) in dry N,N-Dimethylformamide (1.00 mL, 12.9 mmol) was added N,N-Diisopropylethylamine (0.0574 mL, 0.330 mmol) followed by 2,2-Dimethylpropanoyl chloride (0.0204 mL, 0.166 mmol). The reaction mixture was stirred for 3 days. The reaction mixture was concentrated and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.65 (s, 1H), 8.19 (d, J=8.8, 2H), 7.48 (d, J=8.8, 2H), 6.16 (t, J=5.5, 1H), 4.61 (s, 2H), 3.81-3.68 (m, 6H), 3.49 (d, J=4.5, 4H), 3.19-3.06 (m, 2H), 2.69 (d, J=12.7, 2H), 1.27 (s, 9H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+467.3 (M+H)+

Workup

concentrationThe reaction mixture was concentrated
custompurified by HPLC

Sources & evidence

ORD record: ord-9bf9252323c3459b96358feff654af08
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163763B2

Reaction notes

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