Dichloromethane → HCID 9866421, compound

HRID 2268952Notes

Reaction equation

HRID 2268952 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([N:6](C)[C:7]2[N:12]=[C:11]([N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[N:15]=[CH:14]3)[CH:10]=[CH:9][N:8]=2)[CH2:2]1.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:32](Cl)Cl>>[C:23]1([NH:29][C:30]([N:1]2[CH2:2][CH2:32][CH:4]([CH2:3][NH:6][C:7]3[N:12]=[C:11]([N:13]4[C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=5[N:15]=[CH:14]4)[CH:10]=[CH:9][N:8]=3)[CH2:5]2)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 7672Phenyl isocyanateHCID 18332644HCID 18332644, compound

Product 1

HCID 9866421HCID 9866421, compound

Procedure

To a solution of 21 mg of 2-[(pyrrolidin-3-yl)-methylamino]-4-[benzimidazol-1-yl]pyrimidine in 1 mL of CH2Cl2 was added 11 mg of phenyl isocyanate. The mixture was stirred at room temperature for 4 h, then concentrated. The residue was purified by flash chromatography, eluting with a gradient system of 1:1 hexanes-acetone to 1:2 hexanes-acetone, to yield 24 mg of the title compound as an off-white foam. 1H NMR (500 MH, CDCl3): δ 8.63 (s, 1H), 8.41 (d, J=4.8, 1H), 8.18 (d, J=7.6 Hz, 1H), 7.87 (dd, J=1.2, 6.9 Hz, 1H), 7.36-7.46 (m, 3H), 7.25-7.32 (m, 2H), 7.03 (dt, J=1.2, 7.3 Hz, 1H), 6.85 (d, J=5.5 Hz, 1H), 6.18 (s, 1H), 5.70 (br s, 1H), 3.46-3.76 (m, 5H), 3.36 (dd, J=6.6, 9.8 Hz, 1H), 2.70-2.81 (m, 1H), 2.17-2.26 (m, 1H), 1.70-1.92 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography
  3. washeluting with a gradient system of 1:1 hexanes-acetone to 1:2 hexanes-acetone

Sources & evidence

ORD record
ord-2f80b67d13594f499493c97c1527a765
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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