Dimethylformamide → HCID 59239133, compound

HRID 1698019Notes

Reaction equation

HRID 1698019 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].Cl[C:30]1[CH:35]=[C:34]([CH:36]2[CH2:38][CH2:37]2)[N:33]=[CH:32][N:31]=1.C(N(CC)C(C)C)(C)C.CN(C)C=O>>[CH:36]1([C:34]2[N:33]=[CH:32][N:31]=[C:30]([N:20]3[CH2:21][CH2:22][C:16]4[C:15]([N:23]5[CH2:24][CH2:25][O:26][CH2:27][CH2:28]5)=[N:14][C:13]([C:10]5[CH:9]=[CH:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:12][CH:11]=5)=[N:18][C:17]=4[CH2:19]3)[CH:35]=2)[CH2:38][CH2:37]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 249021404-Chloro-6-cyclopropylpyrimidineHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 59239133HCID 59239133, compound

Procedure

1-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0597 g, 0.156 mmol), 4-chloro-6-cyclopropylpyrimidine (0.046 g, 0.30 mmol), N,N-Diisopropylethylamine (0.0570 mL, 0.327 mmol), and dry N,N-Dimethylformamide (0.84 mL, 11 mmol) were combined, the reaction was microwaved on 200 watts, 120° C. for 20 minutes on a CEM microwave. The reaction mixture was purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.70 (s, 1H), 8.37 (s, 1H), 8.21 (d, J=8.8, 2H), 7.50 (d, J=8.8, 2H), 6.91 (s, 1H), 6.21 (t, J=5.5, 1H), 4.70 (s, 2H), 3.88 (s, 2H), 3.73 (d, J=4.5, 4H), 3.48 (d, J=4.3, 4H), 3.16-3.08 (m, 2H), 2.75 (s, 2H), 2.01-1.91 (m, 1H), 1.06 (t, J=7.2, 3H), 1.02-0.88 (m, 4H). LC/MS-m/z+501.2 (M+H)+.

Workup

  1. customthe reaction was microwaved on 200 watts, 120° C. for 20 minutes on a CEM microwave
  2. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-e67a528cfbd64f918c3d3198b66ddf91
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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