Methylamine → 2-(3-Dimethylamino-propylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methylamide
Reaction equation
[CH3:1][NH2:2].C(O[C:6]([C:8]1[C:9](=[O:34])[C:10]2[CH:15]=[N:14][C:13]([NH:16][CH2:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])=[N:12][C:11]=2[N:23]([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[CH2:30][CH2:29][CH2:28]3)[CH:24]=1)=[O:7])C>>[CH3:1][NH:2][C:6]([C:8]1[C:9](=[O:34])[C:10]2[CH:15]=[N:14][C:13]([NH:16][CH2:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])=[N:12][C:11]=2[N:23]([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[CH2:30][CH2:29][CH2:28]3)[CH:24]=1)=[O:7]Participants
Procedure
A solution of methylamine (1N, 1 mL in methanol) was added to 2-(3-dimethylamino-propylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (Example 6 Step A, 6 mg, 0.015 mmol). The mixture was kept in a sealed tube at 110° C. with stirring for 2 days. The solution, after cooling down to room temperature, was loaded to HPLC for purification (32 mL/min 5-100% MeCN/H2O gradient over 10 min). 2-(3-Dimethylamino-propylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methylamide was obtained as a white solid (4.5 mg, 77%). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.70 (br, 1H), 9.26 (s, 1H), 8.75 (s, 1H), 7.31 (d, J=7.8 Hz, 1H), 7.22 (s, 1H), 7.15 (d, J=7.8 Hz, 1H), 6.86 (br, 1H), 2.99 (m, 9H), 2.25-2.10 (m, 10H), 1.62 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C23H28N6O2: 421.23 (M+H). Found. 421.1
Workup
- customThe mixture was kept in a sealed tube at 110° C.
- customwas loaded to HPLC for purification (32 mL/min 5-100% MeCN/H2O gradient over 10 min)
Sources & evidence
- ORD record
- ord-f01a3334192e489f87d7b57eca61d2a1
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728003B2
Reaction notes
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