Acetonitrile → 2-{4-Methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-ylamino}-ethanol

HRID 32364

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1.I[CH:25]([OH:27])[CH3:26].C(N=C1CCN(C)P(N(CC)CC)N1C)(C)(C)C.CC#N>CN(C=O)C.C(O)(C(F)(F)F)=O>[CH3:7][C:5]1[N:6]=[C:2]([NH:1][CH2:26][CH2:25][OH:27])[S:3][C:4]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[N:9]=1

Participants

Conditions

Temperature: 124 °C

Procedure

To a mixture of [4-(2-amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(3-nitro-phenyl)-amine (0.33 g, 1.0 mmol) and iodoethanol (0.44 g, 2.6 mmol) in dry DMF (2 mL) was added tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3-diazaphosphorine (0.5 mL). The reaction mixture was heated at 124° C. for 20 h. The product was isolated as a brown solid by preparative RP-HPLC (Vydac 218TP1022, 9 mL/min) using a gradient from 10-70% MeCN in 0.1% aq CF3COOH over 40 min. Anal. RP-HPLC: tR=14.30 min (Vydac 218TP54, 0-60% MeCN in 0.1% aq CF3COOH over 20 min, 1 mL/min, 25° C., purity >97%). 1H-NMR (CD3OD) δ: 3.30 (s, 3H, CH3), 3.91 (t, 2H, J=4.6 Hz, CH2), 4.25 (t, 2H, J=4.6 Hz, CH2), 7.21(d, 1H, J=5.2 Hz, pyrimidinyl-H), 7.54 (m, 1H, Ph-H), 7.89 (m, 2H, Ph-H), 8.59 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 8.90 (s, 1H, Ph-H).

Workup

customThe product was isolated as a brown solid by preparative RP-HPLC (Vydac 218TP1022, 9 mL/min)
customover 40 min

Sources & evidence

ORD record: ord-180275eddee24ecfad2c9fbdc01cfca1
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427627B2

Linked notes

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