Water → 2-Amino-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3h)-one

HRID 1013867

Reaction equation

HRID 1013867 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:15][CH2:14][CH2:13][CH2:12][C:5]=2[C:6]=1[C:7](OCC)=[O:8].ClC1C=CC=C2C=1C1C(=O)NC(NC(=O)C(C)(C)C)=[N:26][C:20]=1[NH:21]2.O.[OH-].[NH4+]>CS(C)(=O)=O>[NH2:21][C:20]1[NH:26][C:7](=[O:8])[C:6]2[C:5]3[CH2:12][CH2:13][CH2:14][CH2:15][C:4]=3[S:3][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylateHCID 135916071HCID 135916071, compound

Product 1

HCID 2901972-Amino-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3h)-oneYield 60%

Reagents, catalysts & solvents 1

HCID 6213Dimethyl SulfoneSolvent

Conditions

Temperature
150 °C

Procedure

To a 50 mL flask was added 4 (225 mg, 1 mmol), 9 (452 mg, 4 mmol) in DMSO2 (500 mg) was heated at 150° C. for 2 h. The mixture was cooled to room temperature. 15 mL water was added and ammonium hydroxide was used to neutralize the suspension. The brown solid was obtained by filtration, Washed with water and dried. The solid was dissolved in methanol and silica gel was added A dry silica gel plug obtained after evaporation. The plug was then loaded on the column and washed with 5% methanol in chloroform. The fractions containing the desired product (TLC) were pooled and evaporated to afford 132 mg (60%) of 10 as a white solid: 1H NMR (DMSO-d6) δ 1.71 (m, 4H), 2.60 (m, 2H), 2.72 (m, 2H), 6.38 (s, 2H), 10.72 (s, 1H). Anal. calcd for C10H11N3OS: C, 54.28; H, 5.01; N, 18.99: O, 7.23; S, 14.49. Found: C, 53.45; H, 5.06; N, 18.26; S, 14.02.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe brown solid was obtained by filtration
  3. washWashed with water
  4. customdried
  5. dissolutionThe solid was dissolved in methanol
  6. additionsilica gel was added A dry silica gel plug
  7. customobtained
  8. customafter evaporation
  9. washwashed with 5% methanol in chloroform
  10. additionThe fractions containing the desired product (TLC)
  11. customevaporated

Sources & evidence

ORD record
ord-8665a481f98345b08eef858ab73d4abe
Source dataset
uspto-grants-2011_07
Patent number
US07982035B2

Linked notes

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