Ethanol → HCID 86633908, compound

HRID 1041035Notes

Reaction equation

HRID 1041035 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[CH2:10]([N:12]1[C:18]2[CH:19]=[C:20]([NH2:23])[CH:21]=[CH:22][C:17]=2[CH2:16][N:15]([CH2:24][CH3:25])[CH2:14][CH2:13]1)[CH3:11].C(O)C>>[Cl:1][C:2]1[N:7]=[C:6]([NH:23][C:20]2[CH:21]=[CH:22][C:17]3[CH2:16][N:15]([CH2:24][CH3:25])[CH2:14][CH2:13][N:12]([CH2:10][CH3:11])[C:18]=3[CH:19]=2)[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2372592,4,5-TrichloropyrimidineHCID 672642811,4-Diethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-8-ylamine

Product 1

HCID 86633908HCID 86633908, compoundYield 65.2%

Conditions

Temperature
80 °C

Procedure

Into a Round bottom flask was added 2,4,5-Trichloro-pyrimidine (0.34 g, 0.0018 mol;), 1,4-Diethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-8-ylamine (0.40 g, 0.0018 mol) and Ethanol (25 mL, 0.43 mol) and was heated at 80° C. for 3 hour. The reaction was evaporated and the residue treated with a sodium carbonate solution, extracted with EtOAc, washed with water, dried and evaporated to give a solid. This was chromatographed on a SiO2 prep plate with DCM/10% ammonia/methanol (10-1) giving (2,5-Dichloro-pyrimidin-4-yl)-(1,4-diethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-8-yl)-amine as a tan solid (0.43 g, 63%). Mp 69-73° C.; LCMS (m/e) 366 (M); 1H-NMR (DMSO, 400 MHz) δ 9.39 (s, 1H), 8.36 (s, 1H), 7.19 (s, 1H), 7.13-7.11 (d, 1H, J=8.08 Hz), 7.05-7.03 (D, 1H, J=7.83 Hz), 3.62 (s, 2H), 3.20-3.15 (q, 3H, J=7.08 Hz), 3.02-2.95 (br, 2H), 2.84-2.76 (br (s, 2H), 2.49-2.40 (br, 2H), 1.20-1.16 (t, 3H, J=7.07 Hz), 1.06-1.02 (t, 3H, J=7.08 Hz).

Workup

  1. customThe reaction was evaporated
  2. additionthe residue treated with a sodium carbonate solution
  3. extractionextracted with EtOAc
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customto give a solid
  8. customThis was chromatographed on a SiO2 prep plate with DCM/10% ammonia/methanol (10-1)

Sources & evidence

ORD record
ord-bc621d71f8894da4a5e4df8578178ea2
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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