Hydrochloric Acid → [(1R,4S)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl]methanol

HRID 986925Notes

Reaction equation

HRID 986925 reaction equation
[NH2:1]C1C(N[C@H]2C[C@@H](CO)C=C2)=NC=NC=1Cl.Cl[C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[C@H:27]1[CH2:31][C@@H:30]([CH2:32][OH:33])[CH:29]=[CH:28]1.Cl>C(OC(OCC)OCC)C>[NH2:1][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[C@H:27]1[CH2:31][C@@H:30]([CH2:32][OH:33])[CH:29]=[CH:28]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86759192(1R,4S)-4-(6-Chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (1R,4S)-4-[(5-Amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol

Product 1

HCID 466400[(1R,4S)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl]methanol

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

(1R,4S)-4-(6-Chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (1R,4S)-4-[(5-Amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol (from part d of this example, 9.63 g, 40.0 mmol), triethylorthoformate (150 mL), and concentrated hydrochloric acid (14 mL) were stirred for 3 hours. Volatiles were evaporated and the residual solid was partitioned between chloroform (300 mL) and saturated aqueous sodium carbonate (100 mL). The aqueous layer was extracted with chloroform (2×100 mL). The combined chloroform layers were dried (sodium sulfate). Volatiles were evaporated under reduced pressure and the residual yellow glass was chromatographed on silica gel. Elution with ethyl acetate gave title compound as white needles from ethyl acetate (7.45 g, 74%), m.p. 121-124° C.; 1H-NMR (DMSO-d6) δ: 8.81 (s, 1H), 8.64 (s, 1H), 6.24 and 6.21 (two m, 2H), 5.75 (m, 1H), 4.75 (t, J=5.4 Hz, 1H), 3.34 (m, 2H), 2.95 (m, 1H), 2.75 (m, 1H), 1.75 (m, 1H).

Workup

  1. customwere stirred for 3 hours
  2. customVolatiles were evaporated
  3. customthe residual solid was partitioned between chloroform (300 mL) and saturated aqueous sodium carbonate (100 mL)
  4. extractionThe aqueous layer was extracted with chloroform (2×100 mL)
  5. dry with materialThe combined chloroform layers were dried (sodium sulfate)
  6. customVolatiles were evaporated under reduced pressure
  7. customthe residual yellow glass was chromatographed on silica gel
  8. washElution with ethyl acetate

Sources & evidence

ORD record
ord-ca0495f387ac4acd87b54475bfd030a1
Source dataset
uspto-grants-2003_10
Patent number
US06630477B1

Reaction notes

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