3-Chloro-4-methoxybenzylamine → HCID 15871163, compound

HRID 1005938Notes

Reaction equation

HRID 1005938 reaction equation
Cl[C:2]1[C:3]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[S:18][C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)[N:7]=1.[S].N1C2SC3CCCCC=3C=2C=NC=1.P(Cl)(Cl)(Cl)=O.CNC.[Cl:47][C:48]1[CH:49]=[C:50]([CH:53]=[CH:54][C:55]=1[O:56][CH3:57])[CH2:51][NH2:52]>CN1CCCC1=O>[Cl:47][C:48]1[CH:49]=[C:50]([CH:53]=[CH:54][C:55]=1[O:56][CH3:57])[CH2:51][NH:52][C:2]1[C:3]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[S:18][C:4]=2[N:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=2)[N:7]=1

Participants

6

Reactant 4

HCID 7380383-Chloro-4-methoxybenzylamineHCID 15871166HCID 15871166, compoundHCID 86587249HCID 86587249, compoundHCID 178527823HCID 178527823, compound

Product 1

HCID 15871163HCID 15871163, compoundYield 125.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 1.5 g of methyl 4-(4-chlorobenzothieno[2, 3-d]pyrimidin-2-yl)phenylcarboxylate (“B”), prepared by dehydrogenation of the corresponding 5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidine compound with sulfur and subsequent chlorination with phosphorus oxychloride/dimethylamine, and 1.5 g of 3-chloro-4-methoxybenzylamine in 20 ml of N-methylpyrrolidone is heated at 110° for 4 hours. After cooling, the mixture is worked up in the customary manner. 2.6 g of methyl 4-[4-(3-chloro-4-methoxybenzylamino)benzothieno[2,3-d]pyrimidin-2-yl]-benzoate, m.p. 203-204°, are obtained.

Workup

  1. temperatureis heated at 110° for 4 hours
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-b395470e5de149769e967ef164341fd8
Source dataset
uspto-grants-2004_09
Patent number
US06787548B1

Reaction notes

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