2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 64554, compound

HRID 904120Notes

Reaction equation

HRID 904120 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[C:17]12([C:27]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[O:28])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2>C(O)CCC>[C:17]12([C:27]([N:29]3[CH2:34][CH2:33][N:32]([C:2]4[N:11]=[C:10]([NH2:12])[C:9]5[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=5)[N:3]=4)[CH2:31][CH2:30]3)=[O:28])[CH2:18][CH:19]3[CH2:20][CH:21]([CH2:22][CH:23]([CH2:25]3)[CH2:24]1)[CH2:26]2

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 17233943(Piperazin-1-yl)(tricyclo[3.3.1.1~3,7~]decan-1-yl)methanone

Product 1

HCID 64554HCID 64554, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-chloro-4-amino-6,7-dimethoxyquinazoline (2.4 g), 1-(1-adamantanecarbonyl)piperazine (2.5 g) and n-butanol (60 ml) was refluxed for 10 hours. After cooling, the solvent was evaporated under reduced pressure, and water was added to the residue. After treating with aqueous ammonia, the precipitated crystals were collected to give crude 2-{4-(1-adamantanecarbonyl)-1-piperazinyl}-4-amino-6,7-dimethoxyquinazoline, m.p. 237°-240° C. Recrystallization from methanol gave pure 2-{4-(1-adamantanecarbonyl)-1-piperazinyl}-4-amino-6,7-dimethoxyquinazoline, m.p. 242°-243° C.

Workup

  1. temperaturewas refluxed for 10 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated under reduced pressure, and water
  4. additionwas added to the residue
  5. additionAfter treating with aqueous ammonia
  6. customthe precipitated crystals were collected
  7. customto give crude 2-{4-(1-adamantanecarbonyl)-1-piperazinyl}-4-amino-6,7-dimethoxyquinazoline, m.p. 237°-240° C
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-bdca86beaa6c435d9c98b3ac7217c123
Source dataset
uspto-grants-1980_10
Patent number
US04230706

Reaction notes

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