3,4-Dichloroaniline → Ethyl 4-[(3,4-dichlorophenyl)amino]-5,7-dihydro-6H-pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidine-6-carboxylate

HRID 38525Notes

Reaction equation

HRID 38525 reaction equation
Cl[C:2]1[C:3]2[C:10]3[CH2:11][N:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[Cl:27])[NH2:23]>>[Cl:19][C:20]1[CH:21]=[C:22]([NH:23][C:2]2[C:3]3[C:10]4[CH2:11][N:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][C:9]=4[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:24]=[CH:25][C:26]=1[Cl:27]

Participants

3

Reactant 2

HCID 72573,4-DichloroanilineHCID 58116864Ethyl12-chloro-7-thia-4,9,11-triazatricyclo[6.4.0.02,6]dodeca-1(8),2(6),9,11-tetraene-4-carboxylate

Product 1

HCID 58116842Ethyl 4-[(3,4-dichlorophenyl)amino]-5,7-dihydro-6H-pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidine-6-carboxylateYield 57%

Procedure

In analogy to Example 22A, the title compound was prepared from ethyl 4-chloro-5,7-dihydro-6H-pyrrolo[3′,4′:4,5]thieno[2,3-d]pyrimidine-6-carboxylate from Example 21A (250 mg, 0.88 mmol) and 3,4-dichloroaniline (150 mg, 0.93 mmol) to yield 324 mg (64% purity, 57% yield), which was used in the next step without purification.

Workup

  1. customto yield 324 mg (64% purity, 57% yield), which
  2. customwas used in the next step without purification

Sources & evidence

ORD record
ord-d1420dc79c4f4f58bd4d85dd5f643ff5
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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