2-Chloropyrimidine → HCID 59239206, compound

HRID 1697890Notes

Reaction equation

HRID 1697890 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:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[C:16]3[CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].Cl[C:29]1[N:34]=[CH:33][CH:32]=[CH:31][N:30]=1>CN(C=O)C>[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:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)[C:16]3[CH2:21][N:20]([C:29]4[N:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 744042-ChloropyrimidineHCID 44816299HCID 44816299, compound

Product 1

HCID 59239206HCID 59239206, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

1-Ethyl-3-(4-(4-morpholino-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (d, 0.15 mmol), chloropyrimidine (0.21 mmol) and i-PrN2Et (0.6 mmol) were mixed in DMF (0.6 mL) in a microwave reaction tube. The mixture was heated to 120° C. and stirred for 15 min. After cooling to room temperature, the mixture was diluted with DMF. The resulting mixture was purified by reverse-phase HPLC to give 1-ethyl-3-(4-(4-morpholino-6-(pyrimidin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (e): 1H NMR (500 MHz, DMSO) δ 8.71 (s, 1H), 8.47 (d, J=4.8, 2H), 8.21 (d, J=8.8, 2H), 7.51 (d, J=8.8, 2H), 6.77 (t, J=2.5, 1H), 6.18 (m, 1H), 4.99 (s, 2H), 4.68 (s, 2H), 3.78 (m, 8H), 3.20-3.15 (m, 2H), 1.26 (t, J=6.9, 3H); LC-MS: m/z=+447 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe resulting mixture was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-eb7526b8887948289fca1d976f784621
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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