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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → t-Butyl 3-(4-(cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxamido)-4-methylphenylcarbamate

HRID 1465029
Notes
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Reaction equation

HRID 1465029 reaction equation
[CH:1]1([NH:4][C:5]2[C:6]3[S:13][CH:12]=[C:11]([C:14]([OH:16])=O)[C:7]=3[N:8]=[CH:9][N:10]=2)[CH2:3][CH2:2]1.[NH2:17][C:18]1[CH:19]=[C:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:21]=[CH:22][C:23]=1[CH3:24].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH:1]1([NH:4][C:5]2[C:6]3[S:13][CH:12]=[C:11]([C:14]([NH:17][C:18]4[CH:19]=[C:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH:21]=[CH:22][C:23]=4[CH3:24])=[O:16])[C:7]=3[N:8]=[CH:9][N:10]=2)[CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 246997865-(Boc-amino)-2-methylanilineHCID 673596884-(Cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxylic acid

Product 1

HCID 67361287t-Butyl 3-(4-(cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxamido)-4-methylphenylcarbamate

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(Cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxylic acid (5.3 g, 22.49 mmol) obtained in Step 3 of Preparation Example 4 was dissolved in DMF (60 mL). t-Butyl 3-amino-4-methylphenylcarbamate (6 g, 26.99 mmol) obtained in Step 2 of Preparation Example 9, EDCI (6.5 g, 33.74 mmol), HOBT (6.1 g, 44.98 mmol) and TEA (4.7 mL, 33.74 mmol) were sequentially added to the reaction mixture, which was stirred at room temperature for 24 hours. After the reaction was completed water (120 mL) was added thereto, and the resulting yellow solid was filtered and dried to obtain the title compound without further purification.

Workup

  1. additionwere sequentially added to the reaction mixture, which
  2. additionwas added
  3. filtrationthe resulting yellow solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-4cb56d8fc38f4893b62dc16e66b15172
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08999973B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes