Hydrochloric Acid → 3-(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)benzoic acid

HRID 2240120Notes

Reaction equation

HRID 2240120 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17].C(N(C(C)C)CC)(C)C.Cl>O1CCCC1.O>[Cl:1][C:2]1[N:3]=[C:4]([NH:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=[O:17])[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74193-Aminobenzoic AcidHCID 81531DiisopropylethylamineHCID 457899672,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine

Product 1

HCID 576001073-(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)benzoic acidYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

0.200 g (0.93 mmol) of 2,4-dichloro-6,7-dihydrothieno[3,2-d]pyrimidine, 0.127 g (0.93 mmol) of 3-aminobenzoic acid, and 0.323 mL (1.85 mmol) of diisopropylethylamine are placed in 4 mL of tetrahydrofuran, stirred for 48 hours at ambient temperature and 48 hours at 70° C. Then the reaction mixture is combined with water and acidified with 1N hydrochloric acid. The precipitate formed is suction filtered and dried. 0.110 g of product I (39%) is obtained.

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-f90b0c3d7700481fb0f6b1660bde9934
Source dataset
uspto-grants-2010_05
Patent number
US07723341B2

Reaction notes

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