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Water → HCID 18768057, compound

HRID 480020
Notes
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Reaction equation

HRID 480020 reaction equation
[Cl:1][CH2:2][CH2:3][C:4](Cl)=[O:5].[NH2:7][C:8]1[CH:28]=[CH:27][C:11]([NH:12][C:13]2[N:18]=[C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:16]([Br:26])=[CH:15][N:14]=2)=[CH:10][CH:9]=1.C(N(CC)CC)C.O>CN(C=O)C>[NH:19]([C:17]1[C:16]([Br:26])=[CH:15][N:14]=[C:13]([NH:12][C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:4](=[O:5])[CH2:3][CH2:2][Cl:1])=[CH:28][CH:27]=2)[N:18]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 693643-Chloropropionyl chlorideHCID 18768043HCID 18768043, compound

Product 1

HCID 18768057HCID 18768057, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Chloropropionyl chloride (0.143 g, 1.13 mmol) was added to a stirred solution of 2-(4-aminoanilino)-4-anilino-5-bromopyrimidine (Method 38; 0.40 g, 1.13 mmol) and triethylamine (0.173 ml, 1.24 mmol) in DMF (1 ml). The mixture was stirred at room temperature and then water (4 ml) was added. The precipitated solid was collected by filtration and washed with ether (1 ml) to give the product (0.21 g, 42%) as a brown solid. MS (MH+): 448, 450.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with ether (1 ml)

Sources & evidence

ORD record
ord-d6e14eea098d45aeac901652717e978c
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06649608B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes