3-Chloroaniline → 4-(3-chloroanilino)-6-ethoxycarbonyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 369863

Reaction equation

HRID 369863 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].C(O)(C)C.CCCCCC>C(O)CCC>[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH:20][C:2]1[C:3]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 21262606Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylateHCID 21585144Isopropanol hexane

Product 1

HCID 212626224-(3-chloroanilino)-6-ethoxycarbonyl-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Under an argon atmosphere, 29.0 g (128 mmol) of 4-chloro-6-ethoxycarbonyl-7H-pyrrolo[2,3-d]pyrimidine and 18.0 ml (171 mmol) of 3-chloro-aniline in 430 ml of n-butanol are stirred at 100° C. for 3 hours (almost dissolved after ≈1 hour, then a thick suspension forms). The reaction mixture is cooled to ~50° C., then 400 ml of isopropanol/hexane (1:1) are added thereto. The reaction mixture is then cooled to RT and the product is filtered off and washed with isopropanol and hexane. Stirring from diethyl ether yields the title compound: 1H-NMR (DMSO-d6) 13.0 and 10.53 (2 sb, 2HN), 8.48 (s, 1H), 8.13 (m, 1H), 7.78 (dm, J=8, 1H), 7.76 (s, 1H), 7.45 (t, J=8, 1H), 7.21 (dm, J=8, 1H), 4.37 (q, J=7, 2H), 1.37 (t, J=7, 3H).

Workup

  1. dissolutionalmost dissolved after ≈1 hour
  2. temperatureThe reaction mixture is cooled to ~50° C.
  3. filtrationthe product is filtered off
  4. washwashed with isopropanol and hexane

Sources & evidence

ORD record
ord-e6cf8974b0ed425bb3de8a192aa716e7
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Linked notes

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