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

HRID 567759Notes

Reaction equation

HRID 567759 reaction equation
[C:1]([C:4]1[NH:20][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:6]=2[CH:5]=1)(O)=[O:2].C[N:22]1CCOCC1.ClC(OCC(C)C)=O.N>C1COCC1.CN1C(=O)N(C)CCC1.O1CCOCC1>[NH2:22][C:1]([C:4]1[NH:20][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:6]=2[CH:5]=1)=[O:2]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformate2×HCID 212626746-carboxy-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 212626756-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 312751,4-DioxaneSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
0 °C

Procedure

Alternative stage 10.1: A mixture of 2.165 g (7.5 mmol) of 6-carboxy-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine in 60 ml of THF and 10 ml of DMPU is heated under reflux for 30 min and then cooled to 0° C., whereupon a fine suspension is obtained. 824 μl (7.5 mmol) of N-methylmorpholine followed by 981 μl (7.5 mmol of isobutyl chloroformate in 10 ml of THF and, after 1 h at 0° C., 824 μl (7.5 mmol) of N-methylmorpholine followed by 981 μl (7.5 mmol) of isobutyl chloroformate again are added dropwise. The mixture is stirred for 1 h and then added dropwise to 70 ml of a saturated solution of ammonia in dioxane. After 3 h, the mixture is concentrated in vacuo. The residue is poured into water, and the precipitate is filtered off and washed with water and boiling isopropanol, whereupon 6-aminocarbonyl-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine is obtained. Further product is obtained from the isopropanol filtrate.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 30 min
  3. customis obtained
  4. additionagain are added dropwise
  5. waitAfter 3 h
  6. concentrationthe mixture is concentrated in vacuo
  7. additionThe residue is poured into water
  8. filtrationthe precipitate is filtered off
  9. washwashed with water

Sources & evidence

ORD record
ord-881df644cf3a42fc92752395e77e9f7b
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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